Substituted thiophene carboxamides and derivatives thereof as microbicides

ABSTRACT

The present disclosure relates to substituted thiophene carboxamides derivatives, their use for controlling phytopathogenic microorganisms and compositions comprising thereof.

CROSS REFERENCE TO RELATED APPLICATIONS

This application is a national stage application under 35 U.S.C. § 371 of International Application No. PCT/EP2020/086743, filed internationally on Dec. 17, 2020, which claims benefit of European Application No.: 19218423.2, filed Dec. 20, 2019.

TECHNICAL FIELD

The present invention relates to substituted thiophene carboxamide derivatives, their use for controlling phytopathogenic microorganisms and compositions comprising thereof.

BACKGROUND

Though numerous microbicidal agents have been developed until now, the need remains for the development of new microbicidal compounds in order to address the ever increasing environmental and economic requirements imposed on modern-day crop protection agents and compositions. This includes, for example, improvement to the spectrum of action, safety profile, selectivity, application rate, formation of residues, and favourable preparation ability. It may also be desired to have new compounds to prevent the emergence of resistance.

The present invention provides new compounds which have advantages over known compounds and compositions in at least some of these aspects.

EP 450355 discloses thiophenecarboxamide derivatives that are useful for protecting plants from attacks by plant-damaging microorganisms.

WO 2004/024692 discloses heterocyclic carboxylic acid derivatives and their use as fungicides and bactericides for protection of plants or materials such as wood.

SUMMARY

The present invention relates compounds of the formula (I) as recited herein as well as their isomers, polymorphs, salts, N-oxides and solvates.

The present invention relates to a composition comprising at least one compound of formula (I) or as defined herein and at least one agriculturally suitable carrier.

The present invention relates to processes for preparing compounds of formula (I) as described herein and intermediates thereof.

The present invention relates to a method for controlling phytopathogenic microorganisms which comprises the step of applying at least one compound of formula (I) as defined herein or a composition as defined herein to the plants, plant parts, seeds, fruits or to the soil in which the plants grow.

Definitions

The term “alkyl” as used herein in the context of alkyl or alkylsulfonyl, alkylsulfinyl, alkylthio, alkylamino, for example, is to be understood as preferably meaning branched and unbranched alkyl, meaning e.g. methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert-butyl, sec-butyl, pentyl, iso-pentyl, hexyl, heptyl, octyl, nonyl and decyl and the isomers thereof.

The term “alkenyl” as used herein is to be understood as preferably meaning branched and unbranched alkenyl, e.g. a vinyl, propen-1-yl, propen-2-yl, but-1-en-1-yl, but-1-en-2-yl, but-2-en-1-yl, but-2-en-2-yl, but-1-en-3-yl, 2-methyl-prop-2-en-1-yl, or 2-methyl-prop-1-en-1-yl group.

The term “alkynyl” as used herein is to be understood as preferably meaning branched and unbranched alkynyl, e.g. an ethynyl, prop-1-yn-1-yl, but-1-yn-1-yl, but-2-yn-1-yl, or but-3-yn-1-yl group.

The term “halogen” or “Hal” as used herein is to be understood as meaning fluorine, chlorine, bromine or iodine.

The term “halo” or “halogeno” (e.g. haloalkyl, “C₁-C₆-haloalkyl” or “C₁-C₈-halogenoalkyl”) designates the optional presence of one or more halogen substituents that may the same or different.

The term “haloalkyl” as used herein is to be understood as preferably meaning branched and unbranched alkyl, as defined supra, in which one or more of the hydrogen substituents is replaced in the same way or differently with halogen. Particularly preferably, said haloalkyl is, e.g. chloromethyl, fluoropropyl, fluoromethyl, difluoromethyl, trichloromethyl, 2,2,2-trifluoroethyl, pentafluoroethyl, bromobutyl, trifluoromethyl, iodoethyl, and isomers thereof.

The term “haloalkenyl” as used herein is to be understood as preferably meaning branched and unbranched alkenyl, as defined supra, in which one or more of the hydrogen substituents is replaced in the same way or differently with halogen.

The term “haloalkynyl” as used herein is to be understood as preferably meaning branched and unbranched alkynyl, as defined supra, in which one or more of the hydrogen substituents is replaced in the same way or differently with halogen.

The term “alkoxy” as used herein refers to a group of formula (alkyl)-O—, in which the term “alkyl” is as defined herein. Examples of C₁-C₈-alkoxy include but are not limited to methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, n-hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy.

The term “halogenalkoxy” as used herein refers to a alkoxy group as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different. Examples of C₁-C₈-halogenoalkoxy include but are not limited to chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy.

The term “alkylsulfanyl” as used herein refers to a saturated, linear or branched group of formula (alkyl)-S—, in which the term “alkyl” is as defined herein. Examples of C₁-C₈-alkylsulfanyl include but are not limited to methylsulfanyl, ethylsulfanyl, propylsulfanyl, isopropylsulfanyl, butylsulfanyl, sec-butylsulfanyl, isobutylsulfanyl, tert-butylsulfanyl, pentylsulfanyl, isopentylsulfanyl, hexylsulfanyl group.

The term “halogenoalkylsulfanyl” as used herein refers to a alkylsulfanyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.

The term “alkylsulfinyl” as used herein refers to a saturated, linear or branched group of formula (alkyl)-S(═O)—, in which the term “alkyl” is as defined herein. Examples of C₁-C₈-alkylsulfinyl include but are not limited to saturated, straight-chain or branched alkylsulfinyl radicals having 1 to 8, preferably 1 to 6 and more preferably 1 to 4 carbon atoms, for example (but not limited to) methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl.

The term “halogenoalkylsulfinyl” as used herein refers to a alkylsulfinyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.

The term “alkylsulfonyl” s used herein refers to a saturated, linear or branched group of formula (alkyl)-S(═O)₂—, in which the term “alkyl” is as defined herein. Examples of C₁-C₈-alkylsulfonyl include but are not limited to methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl.

The term “halogenoalkylsulfonyl” as used herein refers to a C₁-C₈-alkylsulfonyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.

The term “alkylcarbonyl” as used herein refers to a saturated, linear or branched group of formula (alkyl)-C(═O)—, in which the term “alkyl” is as defined herein.

The term “halogenoalkylcarbonyl” as used herein refers to a alkylcarbonyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.

The term “alkoxycarbonyl” as used herein refers to a saturated, linear or branched group of formula (alkoxy)-C(═O)—, in which the term “alkoxy” is as defined herein.

The term “haloalkoxycarbonyl” as used herein refers to an alkoxycarbonyl as defined above in which one or more hydrogen atoms are replaced with one or more halogen atoms that may be the same or different.

The term “cycloalkyl” as used herein refers to a non-aromatic monocyclic carbon containing ring, having 3 to 8 carbon atoms. Examples of saturated cycloalkyl include but are not limited to cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl and cyclodecyl group.

The term “heterocyclyl” as used herein refers to four-, five- or six-membered, saturated or partially unsaturated heterocycles containing one to four heteroatoms independently selected from the group of oxygen, nitrogen and sulfur. If the ring contains more than one oxygen atom, they are not directly adjacent.

The term “aryl” as used herein refers to an aromatic, hydrocarbon, ring system, comprising from 6 to 15 carbon atoms, or from 6 to 12 carbon atoms, preferably from 6 to 10 carbon atoms. The ring system may be monocyclic or fused polycyclic (e.g. bicyclic or tricyclic) aromatic ring system. Examples of aryl include but are not limited to phenyl, azulenyl, naphthyl and fluorenyl. It is further understood that when said aryl group is substituted with one or more substituents, said substituent(s) may be at any positions on said aryl ring(s). Particularly, in the case of aryl being a phenyl group, said substituent(s) may occupy one or both ortho positions, one or both meta positions, or the para position, or any combination of these positions. This definition also applies to aryl as part of a composite substituent (e.g. aryloxy).

The term “aralkyl” as used herein refers to a C₁-C₆-alkyl substituted by an aryl as defined herein. Example of aralkyl includes the benzyl group (—CH₂—C₆H₅).

The term “aromatic 5- to 14-membered heterocycle” or “heteroaryl” as used herein refers to an aromatic ring system comprising 1 to 4 heteroatoms independently selected from the group consisting of oxygen, nitrogen and sulfur. Aromatic heterocycles include aromatic 5- or 6-membered monocyclic heterocycles and 6- to 14-membered polycyclic (e.g. bicyclic or tricyclic) aromatic heterocycles. The 5- to 14-membered aromatic heterocycle can be connected to the parent molecular moiety through any carbon atom or nitrogen atom contained within the heterocycle.

As used herein, the term “C₁-C₆”, e.g. in the context of the definition of “C₁-C₆-alkyl”, or “C₁-C₆-alkoxy”, is to be understood as meaning a group having a finite number of carbon atoms of 1 to 6, i.e. 1, 2, 3, 4, 5, or 6 carbon atoms.

As used herein, the term “C₁-C₈”, e.g. in the context of the definition of “C₁-C₈-alkyl”, or “C₁-C₈-alkoxy”, is to be understood as meaning a group having a finite number of carbon atoms of 1 to 8, i.e. 1, 2, 3, 4, 5, 6, 7 or 8 carbon atoms.

The term “oxo” as used herein refers to an oxygen atom which is bound to a carbon atom or sulfur atom via a double bound.

The term “leaving group” as used herein is to be understood as meaning a group which is displaced from a compound in a substitution or an elimination reaction, for example a halogen atom, a trifluoromethanesulfonate (“triflate”) group, alkoxy, methanesulfonate, p-toluenesulfonate, etc.

DETAILED DESCRIPTION

The present invention relates to compounds of formula (I):

wherein

-   -   R¹ and R² are identical and are chlorine or bromine;     -   R³ is methyl;     -   R⁴ and R⁵ are selected independently from one another from the         group consisting of hydrogen, halogen, cyano, hydroxyl,         C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl,         —O—C(═O)—C₁-C₆-alkyl, C₃-C₆-carbocycle, 4-, 5- or 6-membered         non-aromatic heterocyclyl, —C(═O)—NH₂, —C(═O)—NH(C₁-C₆-alkyl),         —C(═O)—N(C₁-C₆-alkyl)₂, —C(═O)—OH, —C(═O)—O—C₁-C₆-alkyl, aryl,         5- to 9-membered heteroaryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy,         —C₁-C₆-alkyl-C₁-C₆-haloalkyl, —C₁-C₆-alkyl-C₃-C₆-carbocycle,         —C₁-C₆-alkyl-4-, 5- or 6-membered non-aromatic heterocyclyl,         —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-hydroxyaryl, —C₁-C₆-alkyl-5- to         9-membered heteroaryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl,         —C₁-C₆-alkyl-S—C(═O)—C₁-C₆-alkyl,         —C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-C(═O)—NH₂,         —C₁-C₆-alkyl-C(═O)—NH(C₁-C₆-alkyl),         —C₁-C₆-alkyl-C(═O)—N(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-C(═O)—OH,         —C₁-C₆-alkyl-C(═O)—O—C₁-C₆-alkyl, —C₁-C₆-alkyl-NH—C(═NH)—NH₂,         —S—C₁-C₆-alkyl, —S—C(═O)—C₁-C₆-alkyl, —S—C(═O)—O—C₁-C₆-alkyl,         —S—C(═S)—O—C₁-C₆-alkyl, —S—C(═O)—S—C₁-C₆-alkyl, —S—C(═O)—NH₂,         —S—C(═O)—NH(C₁-C₆-alkyl), —S—C(═O)—NH(C₁-C₆-alkyl)₂,         —S—C(═S)—NH₂, —S—C(═S)—NH(C₁-C₆-alkyl),         —S—C(═S)—NH(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-S—C(═O)—O—C₁-C₆-alkyl,         —C₁-C₆-alkyl-S—C(═O)—S—C₁-C₆-alkyl, —C₁-C₆-alkyl-S—C(═O)—NH₂,         —C₁-C₆-alkyl-S—C(═O)—NH(C₁-C₆-alkyl),         —C₁-C₆-alkyl-S—C(═O)—NH(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-S—C(═S)—NH₂,         —C₁-C₆-alkyl-S—C(═S)—NH(C₁-C₆-alkyl),         —C₁-C₆-alkyl-S—C(═S)—NH(C₁-C₆-alkyl)₂, wherein acyclic R⁴, R⁵         radicals may be substituted with one or more R^(w) substituents,         wherein cyclic R⁴, R⁵ radicals may be substituted with one or         more R^(x) substituents, wherein at least one of R⁴ and R⁵ is         hydrogen, C₁-C₆-alkyl or C₃-C₆-carbocycle, or R⁴ and R⁵ form         together with the carbon atom to which they are attached a         carbonyl, a thiocarbonyl, a C₃-C₆-carbocycle or a 3- to         6-membered heterocycle, wherein said C₃-C₆-carbocycle and 3- to         6-membered heterocycle may be substituted with one or more R^(x)         substituents, wherein R^(w) is independently selected from the         group consisting of nitro, hydroxyl, cyano, carboxyl, amino,         sulfanyl, pentafluoro-λ⁶-sulfanyl, formyl, carbamoyl, carbamate,         C₃-C₇-cycloalkyl, C₃-C₇-halogenocycloalkyl having 1 to 5 halogen         atoms, C₁-C₈-alkylamino, di-C₁-C₈-alkylamino, C₁-C₈-alkoxy,         C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms,         C₁-C₈-alkylsulfanyl, C₁-C₈-halogenoalkylsulfanyl having 1 to 5         halogen atoms, C₁-C₈-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl         having 1 to 5 halogen atoms, C₁-C₈-alkylcarbamoyl,         di-C₁-C₈-alkylcarbamoyl, C₁-C₈-alkoxycarbonyl,         C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms,         C₁-C₈-alkylcarbonyloxy, C₁-C₈-halogenoalkylcarbonyloxy having 1         to 5 halogen atoms, C₁-C₈-alkylcarbonylamino,         C₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms,         C₁-C₈-alkylsulfinyl, C₁-C₈-halogenoalkylsulfinyl having 1 to 5         halogen atoms, C₁-C₈-alkylsulfonyl, C₁-C₈-halogenoalkylsulfonyl         having 1 to 5 halogen atoms; C₁-C₈-alkylsulfonylamino,         C₁-C₈-halogenoalkylsulfonylamino having 1 to 5 halogen atoms;         sulfamoyl; C₁-C₈-alkylsulfamoyl and di-C₁-C₈-alkylsulfamoyl,         wherein R^(x) is independently selected from the group         consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amino,         sulfanyl, pentafluoro-λ⁶-sulfanyl, formyl, carbamoyl, carbamate,         C₁-C₈-alkyl, C₃-C₇-cycloalkyl, C₁-C₈-halogenoalkyl having 1 to 5         halogen atoms, C₃-C₇-halogenocycloalkyl having 1 to 5 halogen         atoms, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-alkylamino,         di-C₁-C₈-alkylamino, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy having 1         to 5 halogen atoms, C₁-C₈-alkylsulfanyl,         C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms,         C₁-C₈-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl having 1 to 5         halogen atoms, C₁-C₈-alkylcarbamoyl, di-C₁-C₈-alkylcarbamoyl,         C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxycarbonyl having 1 to 5         halogen atoms, C₁-C₈-alkylcarbonyloxy,         C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms,         C₁-C₈-alkylcarbonylamino, C₁-C₈-halogenoalkylcarbonylamino         having 1 to 5 halogen atoms, C₁-C₈-alkylsulfanyl,         C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms,         C₁-C₈-alkylsulfinyl, C₁-C₈-halogenoalkylsulfinyl having 1 to 5         halogen atoms, C₁-C₈-alkylsulfonyl, C₁-C₈-halogenoalkylsulfonyl         having 1 to 5 halogen atoms; C₁-C₈-alkylsulfonylamino,         C₁-C₈-halogenoalkylsulfonylamino having 1 to 5 halogen atoms;         sulfamoyl; C₁-C₈-alkylsulfamoyl and di-C₁-C₈-alkylsulfamoyl;     -   R⁶ and R⁷ are independently selected from the group consisting         of hydrogen, C₁-C₆-alkyl, C₃-C₆-carbocycle; or R⁶ and R⁷ form         together with the carbon atom to which they are attached a         C₃-C₆-carbocycle or a 3- to 6-membered heterocycle;     -   n is 0 or 1;     -   W is oxygen or sulfur;     -   Y is NR⁸ with R⁸ being hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-cyanoalkyl, hydroxy, C₁-C₆-alkoxy or C₃-C₆-carbocycle;     -   Z is selected from the group consisting of cyano, —C(═O)—OR^(a),         —C(═O)—SR^(a), —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c) or         —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a), wherein R^(a) is selected         from the group consisting of hydrogen, C₁-C₆-alkyl,         C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,         C₃-C₈-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered         non-aromatic heterocyclyl, —C₁-C₆-alkyl-Si(C₁-C₆-alkyl)₃,         —C₁-C₆-alkyl-C₃-C₈-cycloalkyl, 5- to 9-membered heteroaryl and         —C₁-C₆-alkyl-5- to 9-membered heteroaryl, or R^(a) can form         together with R⁴ and with the atoms to which they are attached,         a 4- to 7-membered heterocycle, R^(b) and R^(c) are         independently selected from the group consisting of hydrogen,         C₁-C₆-alkyl, hydroxyl, C₁-C₆-alkoxy, cyano, C₁-C₆-cyanoalkyl, or         R^(b) can form together with R⁴ and with the atoms to which they         are attached, a 4- to 7-membered heterocycle, R^(d) and R^(e)         are independently selected from the group consisting of         hydrogen, cyano, hydroxyl, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl,         C₁-C₆-alkoxy, —O—C(═O)—C₁-C₆-alkyl, C₃-C₆-carbocycle,         —C(═O)—NH₂, —C(═O)—NH(C₁-C₆-alkyl), —C(═O)—N(C₁-C₆-alkyl)₂,         —C(═O)—OH, —C(═O)—O—C₁-C₆-alkyl, aryl, 5- to 9-membered         heteroaryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy,         —C₁-C₆-alkyl-C₃-C₆-carbocycle, —C₁-C₆-alkyl-aryl,         —C₁-C₆-alkyl-hydroxyaryl, —C₁-C₆-alkyl-5- to 9-membered         heteroaryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl,         —C₁-C₆-alkyl-S—C(═O)—C₁-C₆-alkyl,         —C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-C(═O)—NH₂,         —C₁-C₆-alkyl-C(═O)—NH(C₁-C₆-alkyl),         —C₁-C₆-alkyl-C(═O)—N(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-C(═O)—OH,         —C₁-C₆-alkyl-C(═O)—O—C₁-C₆-alkyl, —C₁-C₆-alkyl-NH—C(═NH)—NH₂,         wherein at least one of R^(d) and R^(e) is hydrogen, C₁-C₆-alkyl         or C₃-C₆-carbocycle, or R^(d) and R^(e) form together with the         carbon atom to which they are attached a carbonyl,         C₃-C₆-carbocycle, or a 3- to 6-membered heterocycle;     -   wherein if W is oxygen, and Y is NH, and n=0, and R⁴ is selected         from the group consisting of hydrogen, C₁-C₆-alkyl,         —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-hydroxyaryl,         —C₁-C₆-alkyl-S—C₁-C₆-alkyl and R⁵ is hydrogen, or R⁴ and R⁵ form         together with the carbon atom to which they are attached a         cyclopropyl, then Z is selected from the group consisting of         cyano, —C(═O)—SR^(a), —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c),         —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a);     -   provided that ethyl         {[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]amino}(phenyl)acetate         and ethyl         {[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}(phenyl)acetate         are excluded.

An embodiment is preferred, wherein R¹ and R² are chlorine, and R³ is a methyl.

Also preferred is an embodiment wherein R¹ and R² are bromine, and R³ is a methyl.

Still another embodiment is preferred, wherein R⁴ and R⁵ are selected independently from one another from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₃-C₆-carbocycle, aryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy, —C₁-C₆-alkyl-C₃-C₆-carbocycle, C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-C(═O)—OH; —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl, wherein acyclic R₄, R₅ radicals may be substituted with one or more R^(w) substituents, wherein cyclic R⁴, R⁵ radicals may be substituted with one or more R^(x) substituents, wherein at least one of R⁴ and R⁵ is hydrogen, C₁-C₆-alkyl or C₃-C₆-carbocycle, or R⁴ and R⁵ form together with the carbon atom to which they are attached a C₃-C₆-carbocycle or a 3- to 6-membered heterocycle, wherein said C₃-C₆-carbocycle and 3- to 6-membered heterocycle may be substituted with one or more R^(x) substituents.

Further preferred is an embodiment, wherein W is oxygen.

According to another preferred embodiment, wherein Y is NR⁸ with R⁸ being C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, hydroxy, C₁-C₆-alkoxy or C₃-C₆-carbocycle, and where, and wherein Y is preferably NR⁸ with R⁸ being hydrogen.

Another embodiment is preferred, wherein Z is selected from the group consisting of cyano, —C(═O)—SR^(a), —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c) or —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a); and wherein Z is preferably Z is —C(═O)—OR^(a)

Still another embodiment is preferred, wherein

-   -   R¹ and R² are chlorine, and R³ is a methyl;     -   R⁴ and R⁵ are selected independently from one another from the         group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl,         C₃-C₆-carbocycle, aryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy,         —C₁-C₆-alkyl-C₃-C₆-carbocycle, C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl,         —C₁-C₆-alkyl-C(═O)—OH; —C₁-C₆-alkyl-aryl,         —C₁-C₆-alkyl-S—C₁-C₆-alkyl, wherein acyclic R₄, R₅ radicals may         be substituted with one or more R^(w) substituents, wherein         cyclic R⁴, R⁵ radicals may be substituted with one or more R^(x)         substituents, wherein at least one of R⁴ and R⁵ is hydrogen,         C₁-C₆-alkyl or C₃-C₆-carbocycle, or R⁴ and R⁵ form together with         the carbon atom to which they are attached a C₃-C₆-carbocycle or         a 3- to 6-membered heterocycle, wherein said C₃-C₆-carbocycle         and 3- to 6-membered heterocycle may be substituted with one or         more R^(x) substituents;     -   W is oxygen;     -   Y is NR⁸ with R⁸ being C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-cyanoalkyl, hydroxy, C₁-C₆-alkoxy or C₃-C₆-carbocycle, and         where, and wherein Y is preferably NR⁸ with R⁸ being hydrogen.     -   Z is selected from the group consisting of cyano, —C(═O)—SR^(a),         —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c) or         —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a); and wherein Z is preferably         Z is —C(═O)—OR^(a)

Still another embodiment is preferred, wherein

-   -   R¹ and R² are bromine, and R³ is a methyl;     -   R⁴ and R⁵ are selected independently from one another from the         group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl,         C₃-C₆-carbocycle, aryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy,         —C₁-C₆-alkyl-C₃-C₆-carbocycle, C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl,         —C₁-C₆-alkyl-C(═O)—OH; —C₁-C₆-alkyl-aryl,         —C₁-C₆-alkyl-S—C₁-C₆-alkyl, wherein acyclic R₄, R₅ radicals may         be substituted with one or more R^(w) substituents, wherein         cyclic R⁴, R⁵ radicals may be substituted with one or more R^(x)         substituents, wherein at least one of R⁴ and R⁵ is hydrogen,         C₁-C₆-alkyl or C₃-C₆-carbocycle, or R⁴ and R⁵ form together with         the carbon atom to which they are attached a C₃-C₆-carbocycle or         a 3- to 6-membered heterocycle, wherein said C₃-C₆-carbocycle         and 3- to 6-membered heterocycle may be substituted with one or         more R^(x) substituents;     -   W is oxygen;     -   Y is NR⁸ with R⁸ being C₁-C₆-alkyl, C₁-C₆-haloalkyl,         C₁-C₆-cyanoalkyl, hydroxy, C₁-C₆-alkoxy or C₃-C₆-carbocycle, and         where, and wherein Y is preferably NR⁸ with R⁸ being hydrogen;     -   Z is selected from the group consisting of cyano, —C(═O)—SR^(a),         —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c) or         —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a); and wherein Z is preferably         Z is —C(═O)—OR^(a).

In some embodiments, when R¹ and R² are chlorine, R³ is a methyl group. In some embodiments, when R¹ and R² are bromine, R³ is a methyl group

In another embodiment R⁴ and R⁵ are selected independently from one another from the group consisting of halogen, cyano, hydroxyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, —O—C(═O)—C₁-C₆-alkyl, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C(═O)—NH₂, —C(═O)—NH(C₁-C₆-alkyl), —C(═O)—N(C₁-C₆-alkyl)₂, —C(═O)—OH, —C(═O)—O—C₁-C₆-alkyl, 5- to 9-membered heteroaryl, —C₁-C₆-alkyl-C₁-C₆-haloalkyl, —C₁-C₆-alkyl-4-, 5- or 6-membered non-aromatic heterocyclyl, —C₁-C₆-alkyl-hydroxyaryl, —C₁-C₆-alkyl-5- to 9-membered heteroaryl, —C₁-C₆-alkyl-S—C(═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-C(═O)—NH₂, —C₁-C₆-alkyl-C(═O)—NH(C₁-C₆-alkyl), —C₁-C₆-alkyl-C(═O)—N(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-C(═O)—O—C₁-C₆-alkyl, —C₁-C₆-alkyl-NH—C(═NH)—NH₂, —S—C₁-C₆-alkyl, —S—C(═O)—C₁-C₆-alkyl, —S—C(═O)—O—C₁-C₆-alkyl, —S—C(═S)—O—C₁-C₆-alkyl, —S—C(═O)—S—C₁-C₆-alkyl, —S—C(═O)—NH₂, —S—C(═O)—NH(C₁-C₆-alkyl), —S—C(═O)—NH(C₁-C₆-alkyl)₂, —S—C(═S)—NH₂, —S—C(═S)—NH(C₁-C₆-alkyl), —S—C(═S)—NH(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-S—C(═O)—O—C₁-C₆-alkyl, —C₁-C₆-alkyl-S—C(═O)—S—C₁-C₆-alkyl, —C₁-C₆-alkyl-S—C(═O)—NH₂, —C₁-C₆-alkyl-S—C(═O)—NH(C₁-C₆-alkyl), —C₁-C₆-alkyl-S—C(═O)—NH(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-S—C(═S)—NH₂, —C₁-C₆-alkyl-S—C(═S)—NH(C₁-C₆-alkyl), —C₁-C₆-alkyl-S—C(═S)—NH(C₁-C₆-alkyl)₂; wherein acyclic R₄, R₅ radicals may be substituted with one or more R^(w) substituents, wherein cyclic R₄, R₅ radicals may be substituted with one or more R^(x) substituents, wherein at least one of R⁴ and R⁵ is hydrogen, C₁-C₆-alkyl or C₃-C₆-carbocycle. In another embodiment R⁴ and R⁵ are selected independently from one another from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₃-C₆-carbocycle, aryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy, —C₁-C₆-alkyl-C₃-C₆-carbocycle, C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-C(═O)—OH; —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl, wherein acyclic R₄, R₅ radicals may be substituted with one or more R^(w) substituents, wherein cyclic R₄, R₅ radicals may be substituted with one or more R^(x) substituents, wherein at least one of R⁴ and R⁵ is hydrogen, C₁-C₆-alkyl or C₃-C₆-carbocycle; or R⁴ and R⁵ form together with the carbon atom to which they are attached a C₃-C₆-carbocycle or a 3- to 6-membered heterocycle, wherein said C₃-C₆-carbocycle and 3- to 6-membered heterocycle may be substituted with one or more R^(x) substituents. In another embodiment R⁴ is hydrogen, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₃-C₆-carbocycle, C(═O)—OH, —C(═O)—O—C₁-C₆-alkyl, —C₁-C₆-alkyl-C₁-C₆-alkoxy, —C₁-C₆-alkyl-C₁-C₆-haloalkyl, —C₁-C₆-alkyl-C₃-C₆-carbocycle, —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-hydroxyaryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl-, —C₁-C₆-alkyl-C(═O)—NH₂, —C₁-C₆-alkyl-C(═O)—OH, —C₁-C₆-alkyl-C(═O)—O—C₁-C₆-alkyl, R₅ is hydrogen, C₁-C₆-alkyl or C₃-C₆-carbocycle; or R⁴ and R⁵ form together with the carbon atom to which they are attached a C₃-C₆-carbocycle. In another embodiment R⁴ is hydrogen, C₁-C₆-alkyl, C₃-C₆-carbocycle, —C₁-C₆-alkyl-C₁-C₆-haloalkyl, —C₁-C₆-alkyl-C₃-C₆-carbocycle, —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-hydroxyaryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl-, R₅ is hydrogen or C₁-C₆-alkyl; or R⁴ and R⁵ form together with the carbon atom to which they are attached a C₃-C₆-carbocycle. In another embodiment R⁴ is hydrogen, C₁-C₆-alkyl, C₃-C₆-carbocycle, —C₁-C₆-alkyl-C₁-C₆-haloalkyl, —C₁-C₆-alkyl-C₃-C₆-carbocycle, —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-hydroxyaryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl-, R₅ is hydrogen or C₁-C₆-alkyl. In another embodiment R⁴ and R⁵ form together with the carbon atom to which they are attached a C₃-C₆-carbocycle or 3- to 6-membered heterocycle. In another embodiment R⁴ and R⁵ form together with the carbon atom to which they are attached a C₃-C₆-carbocycle. In another embodiment R⁴ and R⁵ form together with the carbon atom to which they are attached a cyclopropyl or cyclobutyl.

In another embodiment n is 0. In another embodiment n is 1.

In another embodiment W is oxygen. In another embodiment W is sulfur.

In another embodiment Y is NR⁸ with R⁸ being hydrogen. In another embodiment Y is NR⁸ with R⁸ being C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, hydroxy, C₁-C₆-alkoxy or C₃-C₆-carbocycle.

In another embodiment Z is selected from the group consisting of cyano, —C(═O)—SR^(a), —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c) or —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a). In another embodiment Z is —C(═O)—OR^(a).

Especially preferred are the exemplified compounds I.1-I.177.

Not encompassed herein are compounds resulting from combinations which are against natural laws and which the person skilled in the art would therefore exclude based on his/her expert knowledge. For instance, ring structures having three or more adjacent oxygen atoms are excluded.

Depending on the nature of the substituents, the compound of formula (I) may be present in the form of different stereoisomers. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention encompasses both pure stereoisomers and any mixture of these isomers. Where a compound can be present in two or more tautomer forms in equilibrium, reference to the compound by means of one tautomeric description is to be considered to include all tautomer forms.

Any of the compounds of the present invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. Geometric isomers by nature of substituents about a double bond or a ring may be present in cis (=Z-) or trans (=E-) form. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions.

The compound of formula (I) can suitably be in its free form, salt form, N-oxide form or solvate form (e.g. hydrate).

Depending on the nature of the substituents, the compound of formula (I) may be present in the form of the free compound and/or a salt thereof, such as an agrochemically active salt.

Agrochemically active salts include acid addition salts of inorganic and organic acids well as salts of customary bases. Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid, phosphoric acid and nitric acid, and acidic salts, such as sodium bisulfate and potassium bisulfate. Useful organic acids include, for example, formic acid, carbonic acid and alkanoic acids such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, saturated or mono- or diunsaturated fatty acids having 6 to 20 carbon atoms, alkylsulfuric monoesters, alkylsulfonic acids (sulfonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylsulfonic acids or aryldisulfonic acids (aromatic radicals, such as phenyl and naphthyl, which bear one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight-chain or branched alkyl radicals having 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which bear one or two phosphonic acid radicals), where the alkyl and aryl radicals may bear further substituents, for example p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2-phenoxybenzoic acid, 2-acetoxybenzoic acid, etc.

Solvates of the compounds of formula (I) or their salts are stoichiometric compositions of the compounds with solvents.

The compounds of formula (I) may exist in multiple crystalline and/or amorphous forms. Crystalline forms include unsolvated crystalline forms, solvates and hydrates.

The present invention relates to any compounds of formula (I) disclosed in table as well as the use thereof in crop protection (i.e. for controlling phytopathogenic fungi and/or bacteria on plants or plant parts).

Another aspect of the present invention relates to a composition comprising at least one compound of formula (I) according to the invention and at least one agriculturally suitable auxiliary.

Another aspect of the present invention relates to a method for controlling bacterial and/or fungal diseases comprising the step of applying at least one compound of formula (I) according to the invention or a composition according to the invention to the plants, plant parts, seeds, fruits or to the soil in which the plants grow.

Another aspect of the present invention relates to the use of a compound according to the invention or a composition according to the invention to control bacterial and/or fungal diseases on plants or plant parts. Preferably they are used to control fungal diseases on plants or plant parts.

Another aspect of the present invention relates to the use of a compound according to the invention or a composition according to the invention to control nematodes on plants or plant parts.

Another aspect of the present invention relates to the use of a compound according to the invention or a composition according to the invention to control viruses on plants or plant parts.

Preferably the compound or composition according to the invention is used against: Diseases caused by powdery mildew pathogens, such as Podosphaera species (e.g. Podosphaera leucotricha), Sphaerotheca species (e.g. Sphaerotheca fuliginea); diseases caused by rust disease pathogens, such as Uromyces species (e.g. Uromyces appendiculatus); diseases caused by pathogens from the group of the Oomycetes, such as Peronospora species (e.g. Peronospora parasitica), Phytophthora species (e.g. Phytophthora infestans), Plasmopara species (e.g. Plasmopara viticola), Pseudoperonospora species (e.g. Pseudoperonospora humuli or Pseudoperonospora cubensis), Pythium species (e.g. Pythium ultimum); leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species (e.g. Alternaria solani), Cercospora species (e.g. Cercospora beticola), Colletotrichum species (e.g. Colletotrichum lindemuthanium), Venturia species (e.g. Venturia inaequalis); diseases caused by bacterial pathogens, for example Xanthomonas species (e.g. Xanthomonas campestris pv. campestris), Pseudomonas species (e.g. Pseudomonas syringae pv. tomato), Erwinia species (e.g. Erwinia amylovora), Liberibacter species (e.g. Liberibacter Candidatus), Ralstonia species (e.g. Ralstonia solanacearum).

According to further aspect of the present invention the compound or composition according to the invention is used plant defense activator. A plant defense inducer according to the invention is a compound or composition which stimulates the plants' own defense system.

Processes for the Preparation of Compounds of Formula (I)

The present invention relates to processes for the preparation of compounds of formula (I). The compounds of formula (I) can be prepared by various routes in analogy to known processes (see references therein), and by one or more of the following synthetic routes described herein below and in the experimental part.

General Synthetic Routes to the Compounds of Formula (I)

Unless indicated otherwise, in the following, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, W, Y, Z and n have the same meaning as given above for compounds of formula (I).

Process A1

Compounds of formula (Ia) as herein-defined can be prepared by a process A1 which comprises the step of reacting a compound of formula (II) or one of its salts with a compound of formula (III) or one of its salts as illustrated by the following reaction scheme:

wherein U¹ is halogen, a hydroxy group or a C₁-C₆-alkoxy group.

When U¹ represents a hydroxy group, process A1 is advantageously conducted in the presence of a condensing agent. Suitable condensing agents may be selected in the non-limited list consisting of acid halide former, such as phosgene, phosphorous tribromide, phosphorous trichloride, phosphorous pentachloride, phosphorous trichloride oxide, oxalyl chloride or thionyl chloride; anhydride former, such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride; carbodiimides, such as N,N′-dicyclohexylcarbodiimide (DCC), N-(3-Dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (EDC) or other customary condensing agents, such as phosphorous pentoxide, polyphosphoric acid, bis(2-oxo-3-oxazolidinyl)phosphinic chloride, 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate (HATU), 2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate (TBTU), (1-cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate, N,N′-carbonyl-diimidazole, 2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ), triphenylphosphine/tetrachloro-methane, 4-(4,6-dimethoxy[1.3.5]-triazin-2-yl)-4-methylmorpholinium chloride hydrate, bis(2-oxo-3-oxazolidinyl)phosphinic chloride (BOP-CI), bromo-tripyrrolidinophosphoniumhexafluorophosphate (PyBroP), 2-chloro-1,3-dimethylimidazolinium chloride (DMC), propanephosphonic anhydride (T3P) and 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H-one (DEPBT).

When U¹ represents halogen, process A1 is advantageously conducted in the presence of an acid binder. Suitable acid binders for carrying out process A1 are in each case all inorganic and organic bases that are customary for such reactions. Preference is given to alkali metal carbonates, such as cesium carbonate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate, alkaline earth metal acetates, such as sodium acetate, potassium acetate, calcium acetate and also tertiary amines, such as trimethylamine, triethylamine, diisopropylethylamine, tributylamine, N,N-dimethylaniline, N-methylpiperidine, N,N-dimethylpyridin-4-amine, diazabicyclooctane (DABCO), diazabicyclo-nonene (DBN) or diazabicycloundecene (DBU), or aromatic bases such as pyridine.

When U¹ represents a C₁-C₆-alkoxy group, process A1 can be conducted with an excess of the amine component, optionally in the presence of a Lewis acid such as trimethylaluminium.

If appropriate, process A1 can be performed in the presence of a base and if appropriate, in the presence of a solvent, preferably under anhydrous conditions.

Suitable solvents for carrying out process A1 are not particularly limited. They can be customary inert organic solvents as long as it is not dissolving the compound to react therewith or exhibit any particular interaction therewith. Preference is given to using optionally halogenated, aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene, decalin, ISOPAR™ E or ISOPAR™ G, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; ureas, such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H-pyrimidinone; esters, such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, or sulfones, such as sulfolane; and a mixture thereof.

Process A1 may be performed in an inert atmosphere such as argon or nitrogen atmosphere. When carrying out process A1, 1 mole or an excess of compound of formula (III) and from 1 to 5 moles of base can be employed per mole of compound of formula (II). It is also possible to employ the reaction components in other ratios. Work-up is carried out by known methods.

Compounds of formula (III) are commercially available or can be prepared by well-known processes (J. Med. Chem. 2018, 61, 8670-8692; Tetrahedron, 44(1), 195-202; 1988, WO2009070485; WO2019086142; Chem. Res. Toxicol. 1990, 3, 118-124; JP49035334; JP49000223; Journal of Organic Chemistry (1989), 54(12), 2940-2949).

Compounds of formula (IIa) wherein U¹ represents a hydroxy group are commercially available, can be prepared from compounds of formula (IIb) wherein U¹ represents a C₁-C₆-alkoxy group by well-known processes such as basic hydrolysis or can be prepared by known processes (Beilstein J. Org. Chem. 2007, 3, No. 23)

Compounds of formula (IIc) wherein U¹ represents a halogen are commercially available or can be prepared from compounds of formula (IIa) wherein U¹ represents a hydroxy group by well-known processes.

Compounds of formula (IIb) wherein U¹ represents a C₁-C₆-alkoxy group can be prepared from compounds of formula (IIa) wherein U¹ represents a hydroxy group by well-known processes.

Process B1

Compounds of formula (Ib) can be prepared by a process B1 from a compound of formula (Ia) by performing a thionation reaction as illustrated in the following reaction scheme:

Process B1 according to the invention is performed in the presence of a thionating agent.

Suitable thionating agents for carrying out process B1 according to the invention can be sulfur (S), sulfhydric acid (H₂S), sodium sulfide (Na₂S), sodium hydrosulfide (NaHS), boron trisulfide (B₂S₃), bis(diethylaluminium) sulfide ((AlEt₂)₂S), ammonium sulfide ((NH₄)₂S), phosphorous pentasulfide (P₂S₅), Lawesson's reagent (2,4-bis(4-methoxyphenyl)-1,2,3,4-dithiadiphosphetane 2,4-disulfide) or a polymer-supported thionating reagent such as described in Journal of the Chemical Society, Perkin 1 (2001), 358, in the optionally presence of a catalytic or stoichiometric or excess amount, quantity of a base such as an inorganic and organic base. Preference is given to using alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate; heterocyclic aromatic bases, such as pyridine, picoline, lutidine, collidine; and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dimethylpyridin-4-amine or N-methyl-piperidine.

Suitable solvents for carrying out process B1 according to the invention can be customary inert organic solvents. Preference is given to using optionally halogenated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin, chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane, ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane or 1,2-diethoxyethane, nitriles, such as acetonitrile, propionitrile, n- or i-butyronitrile or benzonitrile, sulfurous solvents, such as sulfolane or carbon disulfide.

When carrying out process B1 according to the invention, 1 mole or an excess of the sulfur equivalent of the thionating agent and from 1 to 3 moles of the base can be employed per mole of the amide reactant (Ia).

It is also possible to employ the reaction components in other ratios. Work-up is carried out by known methods.

Process C1

Compounds of formula (I) can be prepared by a process C1 which comprises the step of reacting a compound of formula (IV) or one of its salts with a compound of formula (V) or one of its salts as illustrated by the following reaction scheme:

wherein U³ is a boron derivative such as a boronic acid, a boronic ester derivative, a potassium trifluoroborate derivative or a halogenometal that can be complexed by 1 to 2 ligands such as a halogenomagnesium or a halogenozinc,

and wherein U² is bromine, iodine, a mesylate group, a tosylate group or a triflate group provided when R¹ and R² are bromine, U² is not bromine.

Process C1 can be performed in the presence of a transition metal catalyst such as palladium and if appropriate, in the presence of a phosphine ligand or a N-heterocyclic carbene ligand, if appropriate, in the presence of a base and if appropriate, in the presence of a solvent according to known processes (WO2012054721, Angew. Chem. Int. Ed. 2017, 56, 1581, Angew. Chem. Int. Ed. 2017, 56, 7078, and cited references therein).

Process C1 can be carried out in the presence of a catalyst, such as a metal salt or complex. Suitable metal derivatives for this purpose are transition metal catalysts such as palladium. Suitable metal salts or complexes for this purpose are for example, palladium chloride, palladium acetate, tetrakis(triphenylphosphine)palladium(0), bis(dibenzylideneacetone)palladium(0), tris(dibenzylideneacetone)dipalladium(0), bis(triphenylphosphine)palladium(II) dichloride, [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), bis(cinnamyl)dichlorodipalladium(II), bis(allyl)-dichlorodipalladium(II), [1,1′-bis(di-tert-butylphosphino)ferrocene]dichloropalladium(II), di-p-iodobis(tri-tert-butylphosphino)dipalladium(I) or di-p-bromobis(tri-tert-butylphosphino)dipalladium(I).

It is also possible to generate a palladium complex in the reaction mixture by separate addition to the reaction of a palladium salt and a ligand or salt, such as triethylphosphine, tri-tert-butylphosphine, tri-tert-butylphosphonium tetrafluoroborate, tricyclohexylphosphine, 2-(dicyclohexylphosphino)biphenyl, 2-(di-tert-butylphosphino)biphenyl, 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)biphenyl, 2-(tert-butylphosphino)-2′-(N,N-dimethylamino)biphenyl, 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl, 2-dicyclohexylphosphino-2,6′-dimethoxybiphenyl, 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl, triphenyl-phosphine, tris-(o-tolyl)phosphine, sodium 3-(diphenylphosphino)benzenesulfonate, tris-2-(methoxy-phenyl)phosphine, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl, 1,4-bis(diphenylphosphino)butane, 1,2-bis(diphenylphosphino) ethane, 1,4-bis(dicyclohexylphosphino)butane, 1,2-bis(dicyclohexylphosphino)-ethane, 2-(dicyclohexylphosphino)-2′-(N,N-dimethylamino)-biphenyl, 1,1′-bis(diphenylphosphino)-ferrocene, (R)-(−)-1-[(S)-2-diphenyl-phosphino)ferrocenyl]ethyldicyclohexylphosphine, tris-(2,4-tert-butyl-phenyl)phosphite, di(1-adamantyl)-2-morpholinophenylphosphine or 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride.

It is also advantageous to choose the appropriate catalyst and/or ligand from commercial catalogues such as “Metal Catalysts for Organic Synthesis” by Strem Chemicals or “Phosphorous Ligands and Compounds” by Strem Chemicals.

Suitable bases for carrying out process C1 can be inorganic and organic bases which are customary for such reactions. Preference is given to using alkaline earth metal or alkali metal hydroxides, such as sodium hydroxide, calcium hydroxide, potassium hydroxide or other ammonium hydroxide derivatives; alkaline earth metal, alkali metal or ammonium fluorides such as potassium fluoride, cesium fluoride or tetrabutylammonium fluoride; alkaline earth metal or alkali metal carbonates, such as sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or cesium carbonate; alkali metal or alkaline earth metal acetates, such as sodium acetate, lithium acetate, potassium acetate or calcium acetate; alkali metal or alkaline earth metal phosphate, such as tripotassium phosphate alkali; alkali metal alcoholates, such as potassium tert-butoxide or sodium tert-butoxide; tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, N,N-dicyclohexylmethylamine, N,N-diisopropylethylamine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU); and also aromatic bases, such as pyridine, picolines, lutidines or collidines.

Suitable solvents for carrying out process C1 can be customary inert organic solvents. Preference is given to using optionally halogen automated aliphatic, alicyclic or aromatic hydrocarbons, such as petroleum ether, pentane, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; ethers, such as diethyl ether, diisopropyl ether, methyl tert-butyl ether, methyl tert-amyl ether, dioxane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,2-dimethoxyethane, 1,2-diethoxyethane or anisole; nitriles, such as acetonitrile, propionitrile, n- or iso-butyronitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; ureas, such as 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; esters, such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, or sulfones, such as sulfolane; and a mixture thereof.

It can also be advantageous to carry out process C1 with a co-solvent such as water or an alcohol such as methanol, ethanol, propanol, isopropanol or tert-butanol.

Process C1 may be performed in an inert atmosphere such as argon or nitrogen atmosphere. When carrying out process C1, 1 mole or an excess of compound of formula (V) and from 1 to 5 moles of base and from 0.01 to 20 mole percent of a palladium complex can be employed per mole of compound of formula (IV). It is also possible to employ the reaction components in other ratios. Work-up is carried out by known methods.

Compounds of formula (V) are commercially available or can be prepared by well-known processes.

Compounds of formula (IVa) wherein W is an oxygen can be prepared by reacting a compound of formula (VI) with a compound of formula (III) in the conditions as described in connection with process A1:

wherein U² and U¹ are as herein-defined.

Compounds of formula (VIa) wherein U² is chlorine, bromine or iodine are commercially available or can be prepared by well-known processes with the similar reaction conditions than the ones disclosed to prepare compounds of formula (II).

Compounds of formula (VIb) wherein U² is a mesylate group, a tosylate group or a triflate group can be prepared by well-known processes from the corresponding compound bearing a hydroxy group at the U₂ position.

Process D1

Compounds of formula (I) as herein defined can be prepared by a process D1 from a compound of formula (VII) or one of its salts by performing a halogenation reaction as illustrated in the following reaction scheme:

wherein U⁴ and U⁵ are independently hydrogen, chlorine or a bromine provided that one of U⁴ or U⁵ is at least hydrogen.

Process D1 can be carried out according to known processes (Angewandte Chemie, International Edition, 52(16), 4440-4444; 2013; ACS Catalysis, 6(11), 7839-7843; 2016; Journal of the American Chemical Society, 2017, 139, 888; Angewandte Chemie, International Edition, 2014, 53, 7928; Journal of the American Chemical Society, 2018, 140, 2789; WO2008156879; WO2012114285; WO2008109786; WO2007098356).

Process D1 is performed in the presence of a halogenation agent and if appropriate, in the presence of a solvent.

Suitable halogenation agents for carrying out process D1 are not particularly limited provided they are used for bromination or chlorination. Examples of bromination agents include bromine, N-bromosuccinimide, 1,2-dibromotetrachloroethane and 1,3-dibromo-5,5-dimethyl-2,4-imidazolidinedione. Examples of chlorination agents include N-chlorosuccinimide, sulfuryl chloride, hexachloroethane, and 1,3-dichloro-5,5-dimethyl-2,4-imidazolidinedione.

Suitable solvents for carrying out process D1 are not particularly limited. They can be customary inert organic solvents as long as it is not dissolving the compound to react therewith or exhibit any particular interaction therewith. Suitable solvents can be for instance the solvents disclosed in connection with process A1. To carry out process D1, it can also be advantageous to use an organic acid such as acetic acid or trifluoroacetic acid as a solvent or a co-solvent. To carry out process D1, it can also be advantageous to use a Lewis acid such as zinc chloride (II) as catalyst. To carry out process D1, it can also be advantageous to use transition metal catalysts such as palladium catalysts. To carry out process D1, it can also be advantageous to use an appropriate organometallic reagent such as n-butyllithium. To carry out process D1, according to known process (WO2020079205), it can also be advantageous to use an appropriate base prior to halogenation, such as n-butyllithium, lithium di-isopropylamine, lithium tetramethylpiperidide, lithium bis(trimethylsilyl)amine, methyllithium or chloro-(2,2,6,6-tetramethyl-1-piperidyl)magnesium and the like, preferably under anhydrous conditions. Optionally lithium chloride can be used in pre-formed combination with these reagents.

Process E1

Compounds of formula (I) as herein-defined can be prepared by a process E1 comprising the step of performing a diazotation of a compound of formula (VIII) or one of its salts followed by an aromatic substitution to provide a compound of formula (I) as illustrated in the following reaction scheme:

wherein U⁶ and U⁷ are independently an amino group, chlorine or bromine provided that one of U⁶ or U⁷ is at least an amino group.

Process E1 can be carried out according to known processes (The Chemistry of diazonium and diazo groups; Saul Patai; Wiley-Interscience; 1978; 288-280 and 645-657; Account of Chemical Research (2018), 51, 496 and cited references therein).

Compounds of formula (VIII) or one of its salts as herein-defined can be prepared by a process comprising the step of reducing a nitro group according to well-known methods (Science of Synthesis: Catalytic Reduction in Organic Synthesis 2; J. G. de Vries, 2018, chapter 2.7: Reduction of Nitro Compounds to Amines, Azo Compounds, Hydroxylamines, and Oximes, and Reduction of N-Oxides to Amines, and references therein) or deprotecting a protected amino group according to well-known methods.

Examples of protecting groups of the amino group include a benzyl group, a 4-methoxybenzyl group, an allyl group, an unsubstituted or substituted C₁-C₆-alkylsulfonyl, a trifluoromethylsulfonyl, an unsubstituted or substituted phenylsulfonyl, an unsubstituted or substituted C₁-C₆-alkoxycarbonyl, an unsubstituted or substituted benzyloxycarbonyl, an allyloxycarbonyl, an acetyl group or a trifluoroacetyl group.

The deprotection process can be carried out according to known processes for removing protecting groups (Greene's Protective Groups in Organic Synthesis; Peter G. M. Wuts; Wiley; Fifth Edition; 2014; 895-1194). For example, tert-butoxycarbonyl and benzyloxycarbonyl protecting groups can be removed in an acidic medium (for example with hydrochloric acid or trifluoroacetic acid). Benzylic protecting groups can be removed hydrogenolytically with hydrogen in the presence of a catalyst (for example palladium on activated carbon). Trifluoroacetyl group can be removed in a basic medium (for example with potassium carbonate or lithium hydroxide).

Compounds of formula (Ic) wherein Z is —C(═O)—OR^(a), wherein R^(a) is selected from the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C₁-C₆-alkyl-Si(C₁-C₆-alkyl)₃, —C₁-C₆-alkyl-C₃-C₈-cycloalkyl, 5- to 9-membered heteroaryl and —C₁-C₆-alkyl-5- to 9-membered heteroaryl can be prepared from compounds of formula (Id) wherein Z is —C(═O)—OR^(a), wherein R^(a) is an hydrogen and corresponding alcohols or one of their salts by well-known coupling process in the conditions as described in connection with process A1.

Compounds of formula (Id) wherein Z is —C(═O)—OR^(a), wherein R^(a) is an hydrogen can be prepared from compounds of formula (Ic) wherein Z is —C(═O)—OR^(a), wherein R^(a) is selected from the group consisting of C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C₁-C₆-alkyl-Si(C₁-C₆-alkyl)₃, —C₁-C₆-alkyl-C₃-C₈-cycloalkyl, 5- to 9-membered heteroaryl and —C₁-C₆-alkyl-5- to 9-membered heteroaryl by well-known processes such as hydrolysis. Examples of hydrolysis reagents include lithium hydroxide, potassium hydroxide, sodium hydroxide, trimethyltin hydroxide. Hydrolysis may be performed as described in WO2008157844; WO2006002099; WO20050256107; Angewandte Chemie, International Edition (2005), 44(9), 1378-1382.

Compounds of formula (Ie) wherein Z is —C(═O)—SR^(a), —C(═O)—NR^(b)R^(c) or —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a) can be prepared from compounds of formula (Id) wherein Z is —C(═O)—OR^(a), wherein R^(a) is hydrogen and corresponding thiols, amines or one of their salts by well-known coupling processes in the conditions as described in connection with process A1.

Compositions and Formulations

The present invention further relates to a composition, in particular a composition for controlling unwanted microorganisms, comprising one or more compounds of formula (I). The composition is preferably is a fungicidal composition.

The composition typically comprises one or more compounds of formula (I) and one or more acceptable carriers, in particular one or more agriculturally acceptable carriers.

A carrier is a solid or liquid, natural or synthetic, organic or inorganic substance that is generally inert. The carrier generally improves the application of the compounds, for instance, to plants, plants parts or seeds. Examples of suitable solid carriers include, but are not limited to, ammonium salts, natural rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite and diatomaceous earth, and synthetic rock flours, such as finely divided silica, alumina and silicates. Examples of typically useful solid carriers for preparing granules include, but are not limited to crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, synthetic granules of inorganic and organic flours and granules of organic material such as paper, sawdust, coconut shells, maize cobs and tobacco stalks. Examples of suitable liquid carriers include, but are not limited to, water, organic solvents and combinations thereof. Examples of suitable solvents include polar and nonpolar organic chemical liquids, for example from the classes of aromatic and nonaromatic hydrocarbons (such as cyclohexane, paraffins, alkylbenzenes, xylene, toluene alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride), alcohols and polyols (which may optionally also be substituted, etherified and/or esterified, such as butanol or glycol), ketones (such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides (such as dimethylformamide), lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide). The carrier may also be a liquefied gaseous extender, i.e. liquid which is gaseous at standard temperature and under standard pressure, for example aerosol propellants such as halohydrocarbons, butane, propane, nitrogen and carbon dioxide. The amount of carrier typically ranges from 1 to 99.99%, preferably from 5 to 99.9%, more preferably from 10 to 99.5%, and most preferably from 20 to 99% by weight of the composition.

The composition may further comprise one or more acceptable auxiliaries which are customary for formulating compositions (e.g. agrochemical compositions), such as one or more surfactants.

The surfactant can be an ionic (cationic or anionic) or non-ionic surfactant, such as ionic or non-ionic emulsifier(s), foam former(s), dispersant(s), wetting agent(s) and any mixtures thereof. Examples of suitable surfactants include, but are not limited to, salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene and/or propylene oxide with fatty alcohols, fatty acids or fatty amines (polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers), substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic esters, taurine derivatives (preferably alkyl taurates), phosphoric esters of polyethoxylated alcohols or phenols, fatty esters of polyols and derivatives of compounds containing sulfates, sulfonates, phosphates (for example, alkylsulfonates, alkyl sulfates, arylsulfonates) and protein hydrolysates, lignosulfite waste liquors and methylcellulose. A surfactant is typically used when the compound of the formula (I) and/or the carrier is insoluble in water and the application is made with water. Then, the amount of surfactants typically ranges from 5 to 40% by weight of the composition.

Further examples of auxiliaries which are customary for formulating agrochemical compositions include water repellents, siccatives, binders (adhesive, tackifier, fixing agent, such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, natural phospholipids such as cephalins and lecithins and synthetic phospholipids, polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose), thickeners, stabilizers (e.g. cold stabilizers, preservatives, antioxidants, light stabilizers, or other agents which improve chemical and/or physical stability), dyes or pigments (such as inorganic pigments, e.g. iron oxide, titanium oxide and Prussian Blue; organic dyes, e.g. alizarin, azo and metal phthalocyanine dyes), antifoams (e.g. silicone antifoams and magnesium stearate), preservatives (e.g. dichlorophene and benzyl alcohol hemiformal), secondary thickeners (cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica), stickers, gibberellins and processing auxiliaries, mineral and vegetable oils, perfumes, waxes, nutrients (including trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc), protective colloids, thixotropic substances, penetrants, sequestering agents and complex formers.

The choice of the auxiliaries is related to the intended mode of application of the compound of the formula (I) and/or on the physical properties. Furthermore, the auxiliaries may be chosen to impart particular properties (technical, physical and/or biological properties) to the compositions or use forms prepared therefrom. The choice of auxiliaries may allow customizing the compositions to specific needs.

The composition may be in any customary form, such as solutions (e.g. aqueous solutions), emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural or synthetic products impregnated with the compound of the invention, fertilizers and also microencapsulations in polymeric substances. The compound of formula (I) may be present in a suspended, emulsified or dissolved form.

The composition may be provided to the end user as ready-for-use formulation, i.e. the compositions may be directly applied to the plants or seeds by a suitable device, such as a spraying or dusting device. Alternatively, the composition may be provided to the end user in the form of concentrates which have to be diluted, preferably with water, prior to use.

The composition can be prepared in conventional manners, for example by mixing the compound formula (I) with one or more suitable auxiliaries, such as disclosed herein above.

The composition contains generally from 0.01 to 99% by weight, from 0.05 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight, most preferably from 1 to 80% by weight of the compound of formula (I).

The compound(s) and composition(s) comprising thereof can be mixed with other active ingredients like fungicides, bactericides, acaricides, nematicides, insecticides, herbicides, fertilizers, growth regulators, safeners or semiochemicals. This may allow to broaden the activity spectrum or to prevent development of resistance. Examples of known fungicides, insecticides, acaricides, nematicides and bactericides are disclosed in the Pesticide Manual, 17^(th) Edition.

The active ingredients specified herein by their Common Name are known and described, for example, in The Pesticide Manual (16^(th) Ed. British Crop Protection Council) or can be searched in the internet (e.g. www.alanwood.net/pesticides).

Where a compound (A) or a compound (B) can be present in tautomeric form, such a compound is understood herein above and herein below also to include, where applicable, corresponding tautomeric forms, even when these are not specifically mentioned in each case.

Examples of fungicides which could be mixed with the compound(s) of formula (I) and the composition of the invention are:

1) Inhibitors of the ergosterol biosynthesis, for example (1.001) cyproconazole, (1.002) difenoconazole, (1.003) epoxiconazole, (1.004) fenhexamid, (1.005) fenpropidin, (1.006) fenpropimorph, (1.007) fenpyrazamine, (1.008) fluquinconazole, (1.009) flutriafol, (1.010) imazalil, (1.011) imazalil sulfate, (1.012) ipconazole, (1.013) metconazole, (1.014) myclobutanil, (1.015) paclobutrazol, (1.016) prochloraz, (1.017) propiconazole, (1.018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetraconazole, (1.023) triadimenol, (1.024) tridemorph, (1.025) triticonazole, (1.026) (1R,2S,5S)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.027) (1S,2R,5R)-5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.028) (2R)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.029) (2R)-2-(1-chlorocyclopropyl)-4-[(1 S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.030) (2R)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.031) (2S)-2-(1-chlorocyclopropyl)-4-[(1R)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.032) (2S)-2-(1-chlorocyclopropyl)-4-[(1 S)-2,2-dichlorocyclopropyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.033) (2S)-2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.034) (R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.035) (S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.036) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (1.037) 1-({(2R,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.038) 1-({(2S,4S)-2-[2-chloro-4-(4-chlorophenoxy)phenyl]-4-methyl-1,3-dioxolan-2-yl}methyl)-1H-1,2,4-triazole, (1.039) 1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.040) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.041) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (1.042) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.043) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.044) 2-[(2R,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.045) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.046) 2-[(2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.047) 2-[(2S,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.048) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.049) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.050) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.051) 2-[2-chloro-4-(2,4-dichlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.052) 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.053) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)butan-2-ol, (1.054) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)pentan-2-ol, (1.055) mefentrifluconazole, (1.056) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.057) 2-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.058) 2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (1.059) 5-(4-chlorobenzyl)-2-(chloromethyl)-2-methyl-1-(1H-1,2,4-triazol-1-ylmethyl)cyclopentanol, (1.060) 5-(allylsulfanyl)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.061) 5-(allylsulfanyl)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.062) 5-(allylsulfanyl)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (1.063) N′-(2,5-dimethyl-4-{[3-(1,1,2,2-tetrafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.064) N′-(2,5-dimethyl-4-{[3-(2,2,2-trifluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.065) N′-(2,5-dimethyl-4-{[3-(2,2,3,3-tetrafluoropropoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.066) N′-(2,5-dimethyl-4-{[3-(pentafluoroethoxy)phenyl]sulfanyl}phenyl)-N-ethyl-N-methylimidoformamide, (1.067) N′-(2,5-dimethyl-4-{3-[(1,1,2,2-tetrafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.068) N′-(2,5-dimethyl-4-{3-[(2,2,2-trifluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.069) N′-(2,5-dimethyl-4-{3-[(2,2,3,3-tetrafluoropropyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.070) N′-(2,5-dimethyl-4-{3-[(pentafluoroethyl)sulfanyl]phenoxy}phenyl)-N-ethyl-N-methylimidoformamide, (1.071) N′-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methylimidoformamide, (1.072) N′-(4-{[3-(difluoromethoxy)phenyl]sulfanyl}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.073) N′-(4-{3-[(difluoromethyl)sulfanyl]phenoxy}-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, (1.074) N′-[5-bromo-6-(2,3-dihydro-1H-inden-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methylimidoformamide, (1.075) N′-{4-[(4,5-dichloro-1,3-thiazol-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylimidoformamide, (1.076) N′-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.077) N′-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.078) N′-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.079) N′-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.080) N′-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.081) ipfentrifluconazole, (1.082) 2-[4-(4-chlorophenoxy)-2-(trifluoromethyl)phenyl]-1-(1H-1,2,4-triazol-1-yl)propan-2-ol, (1.083) 2-[6-(4-bromophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.084) 2-[6-(4-chlorophenoxy)-2-(trifluoromethyl)-3-pyridyl]-1-(1,2,4-triazol-1-yl)propan-2-ol, (1.085) 3-[2-(1-chlorocyclopropyl)-3-(3-chloro-2-fluoro-phenyl)-2-hydroxy-propyl]imidazole-4-carbonitrile, (1.086) 4-[[6-[rac-(2R)-2-(2,4-difluorophenyl)-1,1-difluoro-2-hydroxy-3-(5-thioxo-4H-1,2,4-triazol-1-yl)propyl]-3-pyridyl]oxy]benzonitrile, (1.087) N-isopropyl-N′-[5-methoxy-2-methyl-4-(2,2,2-trifluoro-1-hydroxy-1-phenylethyl)phenyl]-N-methylimidoformamide, (1.088) N′-{5-bromo-2-methyl-6-[(1-propoxypropan-2-yl)oxy]pyridin-3-yl}-N-ethyl-N-methylimidoformamide, (1.089) methyl 2-[2-chloro-4-(4-chlorophenoxy)phenyl]-2-hydroxy-3-(1H-1,2,4-triazol-1-yl)propanoate.

2) Inhibitors of the respiratory chain at complex I or II, for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr, (2.009) Isofetamid, (2.010) isopyrazam (anti-epimeric enantiomer 1R,4S,9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S,4R,9R), (2.012) isopyrazam (anti-epimeric racemate 1RS,4SR,9SR), (2.013) isopyrazam (mixture of syn-epimeric racemate 1RS,4SR,9RS and anti-epimeric racemate 1RS,4SR,9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1R,4S,9R), (2.015) isopyrazam (syn-epimeric enantiomer 1S,4R,9S), (2.016) isopyrazam (syn-epimeric racemate 1RS,4SR,9RS), (2.017) penflufen, (2.018) penthiopyrad, (2.019) pydiflumetofen, (2.020) Pyraziflumid, (2.021) sedaxane, (2.022) 1,3-dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.023) 1,3-dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.024) 1,3-dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.025) 1-methyl-3-(trifluoromethyl)-N-[2′-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (2.026) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide, (2.027) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)-1H-pyrazole-4-carboxamide, (2.028) inpyrfluxam, (2.029) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1H-pyrazole-4-carboxamide, (2.030) fluindapyr, (2.031) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.032) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (2.033) 5,8-difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.034) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.035) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.036) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.037) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.038) isoflucypram, (2.039) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.040) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.041) N-[1-(2,4-dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.042) N-[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.043) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.044) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.045) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (2.046) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.047) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.048) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carbothioamide, (2.049) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.050) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5-fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.051) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.052) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.053) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.054) N-cyclopropyl-N-(2-cyclopropyl-5-fluorobenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.055) N-cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.056) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (2.057) pyrapropoyne, (2.058) N-[rac-(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.059) N-[(1S,2S)-2-(2,4-dichlorophenyl)cyclobutyl]-2-(trifluoromethyl)nicotinamide, (2.060) flubeneteram.

3) Inhibitors of the respiratory chain at complex III, for example (3.001) ametoctradin, (3.002) amisulbrom, (3.003) azoxystrobin, (3.004) coumethoxystrobin, (3.005) coumoxystrobin, (3.006) cyazofamid, (3.007) dimoxystrobin, (3.008) enoxastrobin, (3.009) famoxadone, (3.010) fenamidone, (3.011) flufenoxystrobin, (3.012) fluoxastrobin, (3.013) kresoxim-methyl, (3.014) metominostrobin, (3.015) orysastrobin, (3.016) picoxystrobin, (3.017) pyraclostrobin, (3.018) pyrametostrobin, (3.019) pyraoxystrobin, (3.020) trifloxystrobin, (3.021) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.022) (2E,3Z)-5-{[1-(4-chlorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.023) (2R)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.024) (2S)-2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide, (3.025) fenpicoxamid, (3.026) mandestrobin, (3.027) N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-formamido-2-hydroxybenzamide, (3.028) (2E,3Z)-5-{[1-(4-chloro-2-fluorophenyl)-1H-pyrazol-3-yl]oxy}-2-(methoxyimino)-N,3-dimethylpent-3-enamide, (3.029) methyl {5-[3-(2,4-dimethylphenyl)-1H-pyrazol-1-yl]-2-methylbenzyl}carbamate, (3.030) metyltetraprole, (3.031) florylpicoxamid.

4) Inhibitors of the mitosis and cell division, for example (4.001) carbendazim, (4.002) diethofencarb, (4.003) ethaboxam, (4.004) fluopicolide, (4.005) pencycuron, (4.006) thiabendazole, (4.007) thiophanate-methyl, (4.008) zoxamide, (4.009) pyridachlometyl, (4.010) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (4.011) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine, (4.012) 4-(2-bromo-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.013) 4-(2-bromo-4-fluorophenyl)-N-(2-bromo-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.014) 4-(2-bromo-4-fluorophenyl)-N-(2-bromophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.015) 4-(2-bromo-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.016) 4-(2-bromo-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.017) 4-(2-bromo-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.018) 4-(2-chloro-4-fluorophenyl)-N-(2,6-difluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.019) 4-(2-chloro-4-fluorophenyl)-N-(2-chloro-6-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.020) 4-(2-chloro-4-fluorophenyl)-N-(2-chlorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.021) 4-(2-chloro-4-fluorophenyl)-N-(2-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.022) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (4.023) N-(2-bromo-6-fluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.024) N-(2-bromophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.025) N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazol-5-amine, (4.026) fluopimomide.

5) Compounds capable to have a multisite action, for example (5.001) bordeaux mixture, (5.002) captafol, (5.003) captan, (5.004) chlorothalonil, (5.005) copper hydroxide, (5.006) copper naphthenate, (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper(2+) sulfate, (5.010) dithianon, (5.011) dodine, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015) metiram, (5.016) metiram zinc, (5.017) oxine-copper, (5.018) propineb, (5.019) sulfur and sulfur preparations including calcium polysulfide, (5.020) thiram, (5.021) zineb, (5.022) ziram, (5.023) 6-ethyl-5,7-dioxo-6,7-dihydro-5H-pyrrolo[3′,4′:5,6][1,4]dithiino[2,3-c][1,2]thiazole-3-carbonitrile.

6) Compounds capable to induce a host defence, for example (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.

7) Inhibitors of the amino acid and/or protein biosynthesis, for example (7.001) cyprodinil, (7.002) kasugamycin, (7.003) kasugamycin hydrochloride hydrate, (7.004) oxytetracycline, (7.005) pyrimethanil, (7.006) 3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline.

8) Inhibitors of the ATP production, for example (8.001) silthiofam.

9) Inhibitors of the cell wall synthesis, for example (9.001) benthiavalicarb, (9.002) dimethomorph, (9.003) flumorph, (9.004) iprovalicarb, (9.005) mandipropamid, (9.006) pyrimorph, (9.007) valifenalate, (9.008) (2E)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (9.009) (2Z)-3-(4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one.

10) Inhibitors of the lipid and membrane synthesis, for example (10.001) propamocarb, (10.002) propamocarb hydrochloride, (10.003) tolclofos-methyl.

11) Inhibitors of the melanin biosynthesis, for example (11.001) tricyclazole, (11.002) tolprocarb.

12) Inhibitors of the nucleic acid synthesis, for example (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).

13) Inhibitors of the signal transduction, for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazid, (13.005) quinoxyfen, (13.006) vinclozolin.

14) Compounds capable to act as an uncoupler, for example (14.001) fluazinam, (14.002) meptyldinocap.

15) Further fungicides selected from the group consisting of (15.001) abscisic acid, (15.002) benthiazole, (15.003) bethoxazin, (15.004) capsimycin, (15.005) carvone, (15.006) chinomethionat, (15.007) cufraneb, (15.008) cyflufenamid, (15.009) cymoxanil, (15.010) cyprosulfamide, (15.011) flutianil, (15.012) fosetyl-aluminium, (15.013) fosetyl-calcium, (15.014) fosetyl-sodium, (15.015) methyl isothiocyanate, (15.016) metrafenone, (15.017) mildiomycin, (15.018) natamycin, (15.019) nickel dimethyldithiocarbamate, (15.020) nitrothal-isopropyl, (15.021) oxamocarb, (15.022) oxathiapiprolin, (15.023) oxyfenthiin, (15.024) pentachlorophenol and salts, (15.025) phosphorous acid and its salts, (15.026) propamocarb-fosetylate, (15.027) pyriofenone (chlazafenone), (15.028) tebufloquin, (15.029) tecloftalam, (15.030) tolnifanide, (15.031) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.032) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethanone, (15.033) 2-(6-benzylpyridin-2-yl)quinazoline, (15.034) dipymetitrone, (15.035) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.036) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-chloro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.037) 2-[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]-1-[4-(4-{5-[2-fluoro-6-(prop-2-yn-1-yloxy)phenyl]-4,5-dihydro-1,2-oxazol-3-yl}-1,3-thiazol-2-yl)piperidin-1-yl]ethanone, (15.038) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.039) 2-{(5R)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.040) 2-{(5S)-3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}-3-chlorophenyl methanesulfonate, (15.041) ipflufenoquin, (15.042) 2-{2-fluoro-6-[(8-fluoro-2-methylquinolin-3-yl)oxy]phenyl}propan-2-ol, (15.043) fluoxapiprolin, (15.044) 2-{3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-4,5-dihydro-1,2-oxazol-5-yl}phenyl methanesulfonate, (15.045) 2-phenylphenol and salts, (15.046) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, (15.047) quinofumelin, (15.048) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.049) 4-oxo-4-[(2-phenylethyl)amino]butanoic acid, (15.050) 5-amino-1,3,4-thiadiazole-2-thiol, (15.051) 5-chloro-N′-phenyl-N′-(prop-2-yn-1-yl)thiophene-2-sulfonohydrazide, (15.052) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidin-4-amine, (15.053) 5-fluoro-2-[(4-methylbenzyl)oxy]pyrimidin-4-amine, (15.054) 9-fluoro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-1,4-benzoxazepine, (15.055) but-3-yn-1-yl {6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.056) ethyl (2Z)-3-amino-2-cyano-3-phenylacrylate, (15.057) phenazine-1-carboxylic acid, (15.058) propyl 3,4,5-trihydroxybenzoate, (15.059) quinolin-8-ol, (15.060) quinolin-8-ol sulfate (2:1), (15.061) tert-butyl {6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate, (15.062) 5-fluoro-4-imino-3-methyl-1-[(4-methylphenyl)sulfonyl]-3,4-dihydropyrimidin-2(1H)-one, (15.063) aminopyrifen, (15.064) (N′-[2-chloro-4-(2-fluorophenoxy)-5-methylphenyl]-N-ethyl-N-methylimidoformamide), (15.065) (N′-(2-chloro-5-methyl-4-phenoxyphenyl)-N-ethyl-N-methylimido-formamide), (15.066) (2-{2-[(7,8-difluoro-2-methylquinolin-3-yl)oxy]-6-fluorophenyl}propan-2-ol), (15.067) (5-bromo-1-(5,6-dimethylpyridin-3-yl)-3,3-dimethyl-3,4-dihydroisoquinoline), (15.068) (3-(4,4-difluoro-5,5-dimethyl-4,5-dihydrothieno[2,3-c]pyridin-7-yl)quinoline), (15.069) (1-(4,5-dimethyl-1H-benzimidazol-1-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline), (15.070) 8-fluoro-3-(5-fluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.071) 8-fluoro-3-(5-fluoro-3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinolone, (15.072) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)-8-fluoroquinoline, (15.073) (N-methyl-N-phenyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide), (15.074) methyl {4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}carbamate, (15.075) (N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}cyclopropanecarboxamide), (15.076) N-methyl-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.077) N-[(E)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.078) N—[(Z)-methoxyiminomethyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.079) N-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]cyclopropanecarboxamide, (15.080) N-(2-fluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.081) 2,2-difluoro-N-methyl-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-acetamide, (15.082) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]acetamide, (15.083) N-[(E)-N-methoxy-C-methyl-carbonimidoyl]-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-benzamide, (15.084) N—[(Z)—N-methoxy-C-methyl-carbonimidoyl]-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.085) N-allyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamide, (15.086) 4,4-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-pyrrolidin-2-one, (15.087) N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzenecarbothioamide, (15.088) 5-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]pyrrolidin-2-one, (15.089) N-((2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3,3,3-trifluoro-propanamide, (15.090) 1-methoxy-1-methyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]-methyl]urea, (15.091) 1,1-diethyl-3-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.092) N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide, (15.093) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide, (15.094) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.095) N-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl)cyclopropanecarboxamide, (15.096) N,2-dimethoxy-N-[[4-[5-(trifluoromethyl}-1,2,4-oxadiazol-3-yl]phenyl]methyl]-propanamide, (15.097) N-ethyl-2-methyl-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl)phenyl]methyl]-propanamide, (15.098) 1-methoxy-3-methyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-methyl]urea, (15.099) 1,3-dimethoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.100) 3-ethyl-1-methoxy-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]urea, (15.101) 1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.102) 4,4-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isooxazolidin-3-one, (15.103) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.104) 3,3-dimethyl-1-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]piperidin-2-one, (15.105) 1-[[3-fluoro-4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]azepan-2-one, (15.106) 4,4-dimethyl-2-[[4-(5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.107) 5,5-dimethyl-2-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]isoxazolidin-3-one, (15.108) ethyl 1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-pyrazole-4-carboxylate, (15.109) N,N-dimethyl-1-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}-1H-1,2,4-triazol-3-amine, (15.110) N-{2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzyl}butanamide, (15.111) N-(1-methylcyclopropyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.112) N-(2,4-difluorophenyl)-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide, (15.113) 1-(5,6-dimethylpyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.114) 1-(6-(difluoromethyl)-5-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.115) 1-(5-(fluoromethyl)-6-methyl-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.116) 1-(6-(difluoromethyl)-5-methoxy-pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.117) 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl dimethylcarbamate, (15.118) N-{4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl}propanamide, (15.119) 3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.120) 9-fluoro-3-[2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.121) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.122) 3-[2-(1-{[3,5-bis(difluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazol-4-yl]-9-fluoro-1,5-dihydro-2,4-benzodioxepin-6-yl methanesulfonate, (15.123) 1-(6,7-dimethylpyrazolo[1,5-a]pyridin-3-yl)-4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline, (15.124) 8-fluoro-N-(4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl)quinoline-3-carboxamide, (15.125) 8-fluoro-N-[(2S)-4,4,4-trifluoro-2-methyl-1-phenylbutan-2-yl]quinoline-3-carboxamide, (15.126) N-(2,4-dimethyl-1-phenylpentan-2-yl)-8-fluoroquinoline-3-carboxamide and (15.127) N-[(2S)-2,4-dimethyl-1-phenylpentan-2-yl]-8-fluoroquinoline-3-carboxamide. All named mixing partners of the classes (1) to (15) can, if their functional groups enable this, optionally form salts with suitable bases or acids.

Another aspect of the present invention relates to one or more of the following compound combinations:

(I.001)+(1.001), (I.001)+(1.002), (I.001)+(1.003), (I.001)+(1.004), (I.001)+(1.005), (I.001)+(1.006), (I.001)+(1.007), (I.001)+(1.008), (I.001)+(1.009), (I.001)+(1.010), (I.001)+(1.011), (I.001)+(1.012), (I.001)+(1.013), (I.001)+(1.014), (I.001)+(1.015), (I.001)+(1.016), (I.001)+(1.017), (I.001)+(1.018), (I.001)+(1.019), (I.001)+(1.020), (I.001)+(1.021), (I.001)+(1.022), (I.001)+(1.023), (I.001)+(1.024), (I.001)+(1.025), (I.001)+(1.026), (I.001)+(1.027), (I.001)+(1.028), (I.001)+(1.029), (I.001)+(1.030), (I.001)+(1.031), (I.001)+(1.032), (I.001)+(1.033), (I.001)+(1.034), (I.001)+(1.035), (I.001)+(1.036), (I.001)+(1.037), (I.001)+(1.038), (I.001)+(1.039), (I.001)+(1.040), (I.001)+(1.041), (I.001)+(1.042), (I.001)+(1.043), (I.001)+(1.044), (I.001)+(1.045), (I.001)+(1.046), (I.001)+(1.047), (I.001)+(1.048), (I.001)+(1.049), (I.001)+(1.050), (I.001)+(1.051), (I.001)+(1.052), (I.001)+(1.053), (I.001)+(1.054), (I.001)+(1.055), (I.001)+(1.056), (I.001)+(1.057), (I.001)+(1.058), (I.001)+(1.059), (I.001)+(1.060), (I.001)+(1.061), (I.001)+(1.062), (I.001)+(1.063), (I.001)+(1.064), (I.001)+(1.065), (I.001)+(1.066), (I.001)+(1.067), (I.001)+(1.068), (I.001)+(1.069), (I.001)+(1.070), (I.001)+(1.071), (I.001)+(1.072), (I.001)+(1.073), (I.001)+(1.074), (I.001)+(1.075), (I.001)+(1.076), (I.001)+(1.077), (I.001)+(1.078), (I.001)+(1.079), (I.001)+(1.080), (I.001)+(1.081), (I.001)+(1.082), (I.001)+(1.083), (I.001)+(1.084), (I.001)+(1.085), (I.001)+(1.086), (I.001)+(1.087), (I.001)+(1.088), (I.001)+(1.089), (I.001)+(2.001), (I.001)+(2.002), (I.001)+(2.003), (I.001)+(2.004), (I.001)+(2.005), (I.001)+(2.006), (I.001)+(2.007), (I.001)+(2.008), (I.001)+(2.009), (I.001)+(2.010), (I.001)+(2.011), (I.001)+(2.012), (I.001)+(2.013), (I.001)+(2.014), (I.001)+(2.015), (I.001)+(2.016), (I.001)+(2.017), (I.001)+(2.018), (I.001)+(2.019), (I.001)+(2.020), (I.001)+(2.021), (I.001)+(2.022), (I.001)+(2.023), (I.001)+(2.024), (I.001)+(2.025), (I.001)+(2.026), (I.001)+(2.027), (I.001)+(2.028), (I.001)+(2.029), (I.001)+(2.030), (I.001)+(2.031), (I.001)+(2.032), (I.001)+(2.033), (I.001)+(2.034), (I.001)+(2.035), (I.001)+(2.036), (I.001)+(2.037), (I.001)+(2.038), (I.001)+(2.039), (I.001)+(2.040), (I.001)+(2.041), (I.001)+(2.042), (I.001)+(2.043), (I.001)+(2.044), (I.001)+(2.045), (I.001)+(2.046), (I.001)+(2.047), (I.001)+(2.048), (I.001)+(2.049), (I.001)+(2.050), (I.001)+(2.051), (I.001)+(2.052), (I.001)+(2.053), (I.001)+(2.054), (I.001)+(2.055), (I.001)+(2.056), (I.001)+(2.057), (I.001)+(2.058), (I.001)+(2.059), (I.001)+(2.060), (I.001)+(3.001), (I.001)+(3.002), (I.001)+(3.003), (I.001)+(3.004), (I.001)+(3.005), (I.001)+(3.006), (I.001)+(3.007), (I.001)+(3.008), (I.001)+(3.009), (I.001)+(3.010), (I.001)+(3.011), (I.001)+(3.012), (I.001)+(3.013), (I.001)+(3.014), (I.001)+(3.015), (I.001)+(3.016), (I.001)+(3.017), (I.001)+(3.018), (I.001)+(3.019), (I.001)+(3.020), (I.001)+(3.021), (I.001)+(3.022), (I.001)+(3.023), (I.001)+(3.024), (I.001)+(3.025), (I.001)+(3.026), (I.001)+(3.027), (I.001)+(3.028), (I.001)+(3.029), (I.001)+(3.030), (I.001)+(3.031), (I.001)+(4.001), (I.001)+(4.002), (I.001)+(4.003), (I.001)+(4.004), (I.001)+(4.005), (I.001)+(4.006), (I.001)+(4.007), (I.001)+(4.008), (I.001)+(4.009), (I.001)+(4.010), (I.001)+(4.011), (I.001)+(4.012), (I.001)+(4.013), (I.001)+(4.014), (I.001)+(4.015), (I.001)+(4.016), (I.001)+(4.017), (I.001)+(4.018), (I.001)+(4.019), (I.001)+(4.020), (I.001)+(4.021), (I.001)+(4.022), (I.001)+(4.023), (I.001)+(4.024), (I.001)+(4.025), (I.001)+(4.026), (I.001)+(5.001), (I.001)+(5.002), (I.001)+(5.003), (I.001)+(5.004), (I.001)+(5.005), (I.001)+(5.006), (I.001)+(5.007), (I.001)+(5.008), (I.001)+(5.009), (I.001)+(5.010), (I.001)+(5.011), (I.001)+(5.012), (I.001)+(5.013), (I.001)+(5.014), (I.001)+(5.015), (I.001)+(5.016), (I.001)+(5.017), (I.001)+(5.018), (I.001)+(5.019), (I.001)+(5.020), (I.001)+(5.021), (I.001)+(5.022), (I.001)+(5.023), (I.001)+(6.001), (I.001)+(6.002), (I.001)+(6.003), (I.001)+(6.004), (I.001)+(7.001), (I.001)+(7.002), (I.001)+(7.003), (I.001)+(7.004), (I.001)+(7.005), (I.001)+(7.006), (I.001)+(8.001), (I.001)+(9.001), (I.001)+(9.002), (I.001)+(9.003), (I.001)+(9.004), (I.001)+(9.005), (I.001)+(9.006), (I.001)+(9.007), (I.001)+(9.008), (I.001)+(9.009), (I.001)+(10.001), (I.001)+(10.002), (I.001)+(10.003), (I.001)+(11.001), (I.001)+(11.002), (I.001)+(12.001), (I.001)+(12.002), (I.001)+(12.003), (I.001)+(12.004), (I.001)+(13.001), (I.001)+(13.002), (I.001)+(13.003), (I.001)+(13.004), (I.001)+(13.005), (I.001)+(13.006), (I.001)+(14.001), (I.001)+(14.002), (I.001)+(15.001), (I.001)+(15.002), (I.001)+(15.003), (I.001)+(15.004), (I.001)+(15.005), (I.001)+(15.006), (I.001)+(15.007), (I.001)+(15.008), (I.001)+(15.009), (I.001)+(15.010), (I.001)+(15.011), (I.001)+(15.012), (I.001)+(15.013), (I.001)+(15.014), (I.001)+(15.015), (I.001)+(15.016), (I.001)+(15.017), (I.001)+(15.018), (I.001)+(15.019), (I.001)+(15.020), (I.001)+(15.021), (I.001)+(15.022), (I.001)+(15.023), (I.001)+(15.024), (I.001)+(15.025), (I.001)+(15.026), (I.001)+(15.027), (I.001)+(15.028), (I.001)+(15.029), (I.001)+(15.030), (I.001)+(15.031), (I.001)+(15.032), (I.001)+(15.033), (I.001)+(15.034), (I.001)+(15.035), (I.001)+(15.036), (I.001)+(15.037), (I.001)+(15.038), (I.001)+(15.039), (I.001)+(15.040), (I.001)+(15.041), (I.001)+(15.042), (I.001)+(15.043), (I.001)+(15.044), (I.001)+(15.045), (I.001)+(15.046), (I.001)+(15.047), (I.001)+(15.048), (I.001)+(15.049), (I.001)+(15.050), (I.001)+(15.051), (I.001)+(15.052), (I.001)+(15.053), (I.001)+(15.054), (I.001)+(15.055), (I.001)+(15.056), (I.001)+(15.057), (I.001)+(15.058), (I.001)+(15.059), (I.001)+(15.060), (I.001)+(15.061), (I.001)+(15.062). (I.001)+(15.063). (I.001)+(15.064). (I.001)+(15.065), (I.001)+15.066), (I.001)+(15.067), (I.001)+(15.068), (I.001)+(15.069), (I.001)+(15.070), (I.001)+(15.071), (I.001)+(15.072), (I.001)+(15.073), (I.001)+(15.074), (I.001)+(15.075), (I.001)+(15.076), (I.001), (I.001)+(15.077), (I.001)+(15.078), (I.001)+(15.079), (I.001)+(15.080), (I.001)+(15.081), (I.001)+(15.082), (I.001)+(15.083), (I.001)+(15.084), (I.001)+(15.085), (I.001)+(15.086), (I.001)+(15.087), (I.001)+(15.088), (I.001)+(15.089), (I.001)+(15.090), (I.001)+(15.091), (I.001)+(15.092), (I.001)+(15.093), (I.001)+(15.094), (I.001)+(15.095), (I.001)+(15.096), (I.001)+(15.097), (I.001)+(15.098), (I.001)+(15.099), (I.001)+(15.100), (I.001)+(15.101), (I.001)+(15.102), (I.001)+(15.103), (I.001)+(15.104), (I.001)+(15.105), (I.001)+(15.106), (I.001)+(15.107), (I.001)+(15.108), (I.001)+(15.109), (I.001)+(15.110), (I.001)+(15.111), (I.001)+(15.112), (I.001)+(15.113), (I.001)+(15.114), (I.001)+(15.115), (I.001)+(15.116), (I.001)+(15.117), (I.001)+(15.118), (I.001)+(15.119), (I.001)+(15.120), (I.001)+(15.121), (I.001)+(15.122), (I.001)+(15.123), (I.001)+(15.124), (I.001)+(15.125), (I.001)+(15.126), (I.001)+(15.127).

In these combinations, the first component is a compound of formula (I) as defined in tables 1a and 1b (e.g. I.001) and the second component is a fungicide chosen in groups 1 to 15 as defined herein. For instance, the combination (I.001)+(I.001) corresponds to a combination comprising compound I.001 in tables 1a and 1b and cyproconazole (I.001).

In some other embodiments, the compound combinations correspond to the above described combinations wherein compound (I.001) is replaced with any one of the compounds recited in tables 1a and 1b.

The compounds of formula (I), and the fungicide selected from groups (1) to (15), can be present in a weight ratio ranging from 100:1 to 1:100 (compound of formula (I): fungicide selected from the groups (1) to (15)), or ranging from 50:1 to 1:50, or ranging from 20:1 to 1:20. Further examples of weight ratio ranges include 95:1 to 1:95, 90:1 to 1:90, 85:1 to 1:85, 80:1 to 1:80, 75:1 to 1:75, 70:1 to 1:70, 65:1 to 1:65, 60:1 to 1:60, 55:1 to 1:55, 45:1 to 1:45, 40:1 to 1:40, 35:1 to 1:35, 30:1 to 1:30, 25:1 to 1:25, 15:1 to 1:15, 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2.

A further fungicide chosen in groups 1 to 15 as defined herein may be added to the compound combinations.

The compounds of formula (I) and compositions comprising thereof may be combined with one or more biological control agents.

Examples of biological control agents which may be combined with the compounds of formula (I) and compositions comprising thereof are:

(A) Antibacterial agents selected from the group of:

(A1) bacteria, such as (A1.1) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661 and described in U.S. Pat. No. 6,060,051); (A1.2) Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ from Certis, US, having accession number FERM BP-8234 and disclosed in U.S. Pat. No. 7,094,592); (A1.3) Bacillus pumilus, in particular strain BU F-33 (having NRRL Accession No. 50185); (A1.4) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available as Taegro® from Novozymes, US); (A1.5) a Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129 and described in International Patent Publication No. WO 2016/154297; and

(A2) fungi, such as (A2.1) Aureobasidium pullulans, in particular blastospores of strain DSM14940; (A2.2) Aureobasidium pullulans blastospores of strain DSM 14941; (A2.3) Aureobasidium pullulans, in particular mixtures of blastospores of strains DSM14940 and DSM14941;

(B) Fungicides selected from the group of:

(1) bacteria, for example (B1.1) Bacillus subtilis, in particular strain QST713/AQ713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661 and described in U.S. Pat. No. 6,060,051); (B1.2) Bacillus pumilus, in particular strain QST2808 (available as SONATA® from Bayer CropScience LP, US, having Accession No. NRRL B-30087 and described in U.S. Pat. No. 6,245,551); (B1.3) Bacillus pumilus, in particular strain GB34 (available as Yield Shield® from Bayer AG, DE); (B1.4) Bacillus pumilus, in particular strain BU F-33 (having NRRL Accession No. 50185); (B1.5) Bacillus amyloliquefaciens, in particular strain D747 (available as Double Nickel™ from Certis, US, having accession number FERM BP-8234 and disclosed in U.S. Pat. No. 7,094,592); (B1.6) Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277); (B1.7) Bacillus amyloliquefaciens strain MBI 600 (available as SUBTILEX from BASF SE); (B1.8) Bacillus subtilis strain GB03 (available as Kodiak® from Bayer AG, DE); (B1.9) Bacillus subtilis var. amyloliquefaciens strain FZB24 (available from Novozymes Biologicals Inc., Salem, Va. or Syngenta Crop Protection, LLC, Greensboro, N.C. as the fungicide TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5); (B1.10) Bacillus mycoides, isolate J (available as BmJ TGAI or WG from Certis USA); (B1.11) Bacillus licheniformis, in particular strain SB3086 (available as EcoGuard™ Biofungicide and Green Releaf from Novozymes); (B1.12) a Paenibacillus sp. strain having Accession No. NRRL B-50972 or Accession No. NRRL B-67129 and described in International Patent Publication No. WO 2016/154297.

In some embodiments, the biological control agent is a Bacillus subtilis or Bacillus amyloliquefaciens strain that produces a fengycin or plipastatin-type compound, an iturin-type compound, and/or a surfactin-type compound. For background, see the following review article: Ongena, M., et al., “Bacillus Lipopeptides: Versatile Weapons for Plant Disease Biocontrol,” Trends in Microbiology, Vol 16, No. 3, March 2008, pp. 115-125. Bacillus strains capable of producing lipopeptides include Bacillus subtilis QST713 (available as SERENADE OPTI or SERENADE ASO from Bayer CropScience LP, US, having NRRL Accession No. B21661 and described in U.S. Pat. No. 6,060,051), Bacillus amyloliquefaciens strain D747 (available as Double Nickel™ from Certis, US, having accession number FERM BP-8234 and disclosed in U.S. Pat. No. 7,094,592); Bacillus subtilis MBI600 (available as SUBTILEX® from Becker Underwood, US EPA Reg. No. 71840-8); Bacillus subtilis Y1336 (available as BIOBAC® WP from Bion-Tech, Taiwan, registered as a biological fungicide in Taiwan under Registration Nos. 4764, 5454, 5096 and 5277); Bacillus amyloliquefaciens, in particular strain FZB42 (available as RHIZOVITAL® from ABiTEP, DE); and Bacillus subtilis var. amyloliquefaciens FZB24 (available from Novozymes Biologicals Inc., Salem, Va. or Syngenta Crop Protection, LLC, Greensboro, N.C. as the fungicide TAEGRO® or TAEGRO® ECO (EPA Registration No. 70127-5); and

(B2) fungi, for example: (B2.1) Coniothyrium minitans, in particular strain CON/M/91-8 (Accession No. DSM-9660; e.g. Contans® from Bayer); (B2.2) Metschnikowia fructicola, in particular strain NRRL Y-30752 (e.g. Shemer®); (B2.3) Microsphaeropsis ochracea (e.g. Microx® from Prophyta); (B2.5) Trichoderma spp., including Trichoderma atroviride, strain SC1 described in International Application No. PCT/IT2008/000196); (B2.6) Trichoderma harzianum rifai strain KRL-AG2 (also known as strain T-22, /ATCC 208479, e.g. PLANTSHIELD T-22G, Rootshield®, and TurfShield from BioWorks, US); (B2.14) Gliocladium roseum, strain 321U from W.F. Stoneman Company LLC; (B2.35) Talaromyces flavus, strain V117b; (B2.36) Trichoderma asperellum, strain ICC 012 from Isagro; (B2.37) Trichoderma asperellum, strain SKT-1 (e.g. ECO-HOPE® from Kumiai Chemical Industry); (B2.38) Trichoderma atroviride, strain CNCM 1-1237 (e.g. Esquive® WP from Agrauxine, FR); (B2.39) Trichoderma atroviride, strain no. V08/002387; (B2.40) Trichoderma atroviride, strain NMI no. V08/002388; (B2.41) Trichoderma atroviride, strain NMI no. V08/002389; (B2.42) Trichoderma atroviride, strain NMI no. V08/002390; (B2.43) Trichoderma atroviride, strain LC52 (e.g. Tenet by Agrimm Technologies Limited); (B2.44) Trichoderma atroviride, strain ATCC 20476 (IMI 206040); (B2.45) Trichoderma atroviride, strain T11 (IMI352941/CECT20498); (B2.46) Trichoderma harmatum; (B2.47) Trichoderma harzianum; (B2.48) Trichoderma harzianum rifai T39 (e.g. Trichodex® from Makhteshim, US); (B2.49) Trichoderma harzianum, in particular, strain KD (e.g. Trichoplus from Biological Control Products, SA (acquired by Becker Underwood)); (B2.50) Trichoderma harzianum, strain ITEM 908 (e.g. Trianum-P from Koppert); (B2.51) Trichoderma harzianum, strain TH35 (e.g. Root-Pro by Mycontrol); (B2.52) Trichoderma virens (also known as Gliocladium virens), in particular strain GL-21 (e.g. SoilGard 12G by Certis, US); (B2.53) Trichoderma viride, strain TV1 (e.g. Trianum-P by Koppert); (B2.54) Ampelomyces quisqualis, in particular strain AQ 10 (e.g. AQ 10® by IntrachemBio Italia); (B2.56) Aureobasidium pullulans, in particular blastospores of strain DSM14940; (B2.57) Aureobasidium pullulans, in particular blastospores of strain DSM 14941; (B2.58) Aureobasidium pullulans, in particular mixtures of blastospores of strains DSM14940 and DSM 14941 (e.g. Botector® by bio-ferm, CH); (B2.64) Cladosporium cladosporioides, strain H39 (by Stichting Dienst Landbouwkundig Onderzoek); (B2.69) Gliocladium catenulatum (Synonym: Clonostachys rosea f. catenulate) strain J1446 (e.g. Prestop® by AgBio Inc. and also e.g. Primastop® by Kemira Agro Oy); (B2.70) Lecanicillium lecanii (formerly known as Verticillium lecanii) conidia of strain KV01 (e.g. Vertalec® by Koppert/Arysta); (B2.71) Penicillium vermiculatum; (B2.72) Pichia anomala, strain WRL-076 (NRRL Y-30842); (B2.75) Trichoderma atroviride, strain SKT-1 (FERM P-16510); (B2.76) Trichoderma atroviride, strain SKT-2 (FERM P-16511); (B2.77) Trichoderma atroviride, strain SKT-3 (FERM P-17021); (B2.78) Trichoderma gamsii (formerly T. viride), strain ICC080 (IMI CC 392151 CABI, e.g. BioDerma by AGROBIOSOL DE MEXICO, S.A. DE C.V.); (B2.79) Trichoderma harzianum, strain DB 103 (e.g., T-Gro 7456 by Dagutat Biolab); (B2.80) Trichoderma polysporum, strain IMI 206039 (e.g. Binab TF WP by BINAB Bio-Innovation AB, Sweden); (B2.81) Trichoderma stromaticum (e.g. Tricovab by Ceplac, Brazil); (B2.83) Ulocladium oudemansii, in particular strain HRU3 (e.g. Botry-Zen® by Botry-Zen Ltd, NZ); (B2.84) Verticillium albo-atrum (formerly V. dahliae), strain WCS850 (CBS 276.92; e.g. Dutch Trig by Tree Care Innovations); (B2.86) Verticillium chlamydosporium; (B2.87) mixtures of Trichoderma asperellum strain ICC 012 and Trichoderma gamsii strain ICC 080 (product known as e.g. BIO-TAM™ from Bayer CropScience LP, US).

Further examples of biological control agents which may be combined with the compounds of formula (I) and compositions comprising thereof are:

bacteria selected from the group consisting of Bacillus cereus, in particular B. cereus strain CNCM I-1562 and Bacillus firmus, strain I-1582 (Accession number CNCM I-1582), Bacillus subtilis strain OST 30002 (Accession No. NRRL B-50421), Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), B. thuringiensis subsp. kurstaki strain HD-1, B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), Pasteuria penetrans, Pasteuria spp. (Rotylenchulus reniformis nematode)-PR3 (Accession Number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), and Streptomyces galbus strain AQ 6047 (Accession Number NRRL 30232);

fungi and yeasts selected from the group consisting of Beauveria bassiana, in particular strain ATCC 74040, Lecanicillium spp., in particular strain HRO LEC 12, Metarhizium anisopliae, in particular strain F52 (DSM3884 or ATCC 90448), Paecilomyces fumosoroseus (now: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accession No. ATCC 20874), and Paecilomyces lilacinus, in particular P. lilacinus strain 251 (AGAL 89/030550);

viruses selected from the group consisting of Adoxophyes orana (summer fruit tortrix) granulosis virus (GV), Cydia pomonella (codling moth) granulosis virus (GV), Helicoverpa armigera (cotton bollworm) nuclear polyhedrosis virus (NPV), Spodoptera exigua (beet armyworm) mNPV, Spodoptera frugiperda (fall armyworm) mNPV, and Spodoptera littoralis (African cotton leafworm) NPV.

bacteria and fungi which can be added as ‘inoculant’ to plants or plant parts or plant organs and which, by virtue of their particular properties, promote plant growth and plant health. Examples are: Agrobacterium spp., Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., in particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., in particular Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., and Streptomyces spp.

plant extracts and products formed by microorganisms including proteins and secondary metabolites which can be used as biological control agents, such as Allium sativum, Artemisia absinthium, azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), Pyrethrum/Pyrethrins, Quassia amara, Quercus, Quillaja, Regalia, “Requiem™ Insecticide”, rotenone, ryania/ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Brassicaceae extract, in particular oilseed rape powder or mustard powder.

Examples of insecticides, acaricides and nematicides, respectively, which could be mixed with the compounds of formula (I) and compositions comprising thereof are:

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example, carbamates, for example alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothiophosphoryl) salicylate, isoxathion, malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

(2) GABA-gated chloride channel blockers, such as, for example, cyclodiene-organochlorines, for example chlordane and endosulfan or phenylpyrazoles (fiproles), for example ethiprole and fipronil.

(3) Sodium channel modulators, such as, for example, pyrethroids, e.g. acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin s-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans-isomer], deltamethrin, empenthrin [(EZ)-(1R)-isomer], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, momfluorothrin, permethrin, phenothrin [(1R)-trans-isomer], prallethrin, pyrethrins (pyrethrum), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)-isomer)], tralomethrin and transfluthrin or DDT or methoxychlor.

(4) Nicotinic acetylcholine receptor (nAChR) competitive modulators, such as, for example, neonicotinoids, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.

(5) Nicotinic acetylcholine receptor (nAChR) allosteric modulators, such as, for example, spinosyns, e.g. spinetoram and spinosad.

(6) Glutamate-gated chloride channel (GluCl) allosteric modulators, such as, for example, avermectins/milbemycins, for example abamectin, emamectin benzoate, lepimectin and milbemectin.

(7) Juvenile hormone mimics, such as, for example, juvenile hormone analogues, e.g. hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

(8) Miscellaneous non-specific (multi-site) inhibitors, such as, for example, alkyl halides, e.g. methyl bromide and other alkyl halides; or chloropicrine or sulfuryl fluoride or borax or tartar emetic or methyl isocyanate generators, e.g. diazomet and metam.

(9) Modulators of Chordotonal Organs, such as, for example pymetrozine or flonicamid.

(10) Mite growth inhibitors, such as, for example clofentezine, hexythiazox and diflovidazin or etoxazole.

(11) Microbial disruptors of the insect gut membrane, such as, for example Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and B.t. plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry1A.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34Ab1/35Ab1.

(12) Inhibitors of mitochondrial ATP synthase, such as, ATP disruptors such as, for example, diafenthiuron or organotin compounds, for example azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.

(13) Uncouplers of oxidative phosphorylation via disruption of the proton gradient, such as, for example, chlorfenapyr, DNOC and sulfluramid.

(14) Nicotinic acetylcholine receptor channel blockers, such as, for example, bensultap, cartap hydrochloride, thiocylam, and thiosultap-sodium.

(15) Inhibitors of chitin biosynthesis, type 0, such as, for example, bistrifluron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

(16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

(17) Moulting disruptor (in particular for Diptera, i.e. dipterans), such as, for example, cyromazine.

(18) Ecdysone receptor agonists, such as, for example, chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

(19) Octopamine receptor agonists, such as, for example, amitraz.

(20) Mitochondrial complex III electron transport inhibitors, such as, for example, hydramethylnone or acequinocyl or fluacrypyrim.

(21) Mitochondrial complex I electron transport inhibitors, such as, for example from the group of the METI acaricides, e.g. fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad or rotenone (Derris).

(22) Voltage-dependent sodium channel blockers, such as, for example indoxacarb or metaflumizone.

(23) Inhibitors of acetyl CoA carboxylase, such as, for example, tetronic and tetramic acid derivatives, e.g. spirodiclofen, spiromesifen and spirotetramat.

(24) Mitochondrial complex IV electron transport inhibitors, such as, for example, phosphines, e.g. aluminium phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, e.g. calcium cyanide, potassium cyanide and sodium cyanide.

(25) Mitochondrial complex II electron transport inhibitors, such as, for example, beta-ketonitrile derivatives, e.g. cyenopyrafen and cyflumetofen and carboxanilides, such as, for example, pyflubumide.

(28) Ryanodine receptor modulators, such as, for example, diamides, e.g. chlorantraniliprole, cyantraniliprole and flubendiamide,

further active compounds such as, for example, Afidopyropen, Afoxolaner, Azadirachtin, Benclothiaz, Benzoximate, Bifenazate, Broflanilide, Bromopropylate, Chinomethionat, Chloroprallethrin, Cryolite, Cyclaniliprole, Cycloxaprid, Cyhalodiamide, Dicloromezotiaz, Dicofol, epsilon-Metofluthrin, epsilon-Momfluthrin, Flometoquin, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprole, Fluhexafon, Fluopyram, Fluralaner, Fluxametamide, Fufenozide, Guadipyr, Heptafluthrin, Imidaclothiz, Iprodione, kappa-Bifenthrin, kappa-Tefluthrin, Lotilaner, Meperfluthrin, Paichongding, Pyridalyl, Pyrifluquinazon, Pyriminostrobin, Spirobudiclofen, Tetramethylfluthrin, Tetraniliprole, Tetrachlorantraniliprole, Tigolaner, Tioxazafen, Thiofluoximate, Triflumezopyrim and iodomethane; furthermore preparations based on Bacillus firmus (I-1582, BioNeem, Votivo), and also the following compounds: 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine (known from WO2006/043635) (CAS 885026-50-6), {1′-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[indol-3,4′-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003/106457) (CAS 637360-23-7), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006/003494) (CAS 872999-66-1), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010052161) (CAS 1225292-17-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from EP2647626) (CAS 1440516-42-6), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004/099160) (CAS 792914-58-0), PF1364 (known from JP2010/018586) (CAS 1204776-60-2), N-[(2E)-1-[(6-chloropyridin-3-yl)methyl]pyridin-2(1H)-ylidene]-2,2,2-trifluoroacetamide (known from WO2012/029672) (CAS 1363400-41-2), (3E)-3-[1-[(6-chloro-3-pyridyl)methyl]-2-pyridylidene]-1,1,1-trifluoro-propan-2-one (known from WO2013/144213) (CAS 1461743-15-6), N-[3-(benzylcarbamoyl)-4-chlorophenyl]-1-methyl-3-(pentafluoroethyl)-4-(trifluoromethyl)-1H-pyrazole-5-carboxamide (known from WO2010/051926) (CAS 1226889-14-0), 5-bromo-4-chloro-N-[4-chloro-2-methyl-6-(methylcarbamoyl)phenyl]-2-(3-chloro-2-pyridyl)pyrazole-3-carboxamide (known from CN103232431) (CAS 1449220-44-3), 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)-benzamide, 4-[5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(trans-1-oxido-3-thietanyl)-benzamide and 4-[(5S)-5-(3,5-dichlorophenyl)-4,5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-2-methyl-N-(cis-1-oxido-3-thietanyl)benzamide (known from WO 2013/050317 A1) (CAS 1332628-83-7), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3, 3,3-trifluoropropyl)sulfinyl]-propanamide, (+)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3, 3,3-trifluoropropyl)sulfinyl]-propanamide and (−)-N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)sulfinyl]-propanamide (known from WO 2013/162715 A2, WO 2013/162716 A2, US 2014/0213448 A1) (CAS 1477923-37-7), 5-[[(2E)-3-chloro-2-propen-1-yl]amino]-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile (known from CN 101337937 A) (CAS 1105672-77-2), 3-bromo-N-[4-chloro-2-methyl-6-[(methylamino)thioxomethyl]phenyl]-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide, (Liudaibenjiaxuanan, known from CN 103109816 A) (CAS 1232543-85-9); N-[4-chloro-2-[[(1,1-dimethylethyl)amino]carbonyl]-6-methylphenyl]-1-(3-chloro-2-pyridinyl)-3-(fluoromethoxy)-1H-Pyrazole-5-carboxamide (known from WO 2012/034403 A1) (CAS 1268277-22-0), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from WO 2011/085575 A1) (CAS 1233882-22-8), 4-[3-[2,6-dichloro-4-[(3,3-dichloro-2-propen-1-yl)oxy]phenoxy]propoxy]-2-methoxy-6-(trifluoromethyl)-pyrimidine (known from CN 101337940 A) (CAS 1108184-52-6); (2E)- and 2(Z)-2-[2-(4-cyanophenyl)-1-[3-(trifluoromethyl)phenyl]ethylidene]-N-[4-(difluoromethoxy)phenyl]-hydrazinecarboxamide (known from CN 101715774 A) (CAS 1232543-85-9); 3-(2,2-dichloroethenyl)-2,2-dimethyl-4-(1H-benzimidazol-2-yl)phenyl-cyclopropanecarboxylic acid ester (known from CN 103524422 A) (CAS 1542271-46-4); (4aS)-7-chloro-2,5-dihydro-2-[[(methoxycarbonyl)[4-[(trifluoromethyl)thio]phenyl]amino]carbonyl]-indeno[1,2-e][1,3,4]oxadiazine-4a(3H)-carboxylic acid methyl ester (known from CN 102391261 A) (CAS 1370358-69-2); 6-deoxy-3-O-ethyl-2,4-di-O-methyl-, 1-[N-[4-[1-[4-(1,1,2,2,2-pentafluoroethoxy)phenyl]-1H-1,2,4-triazol-3-yl]phenyl]carbamate]-α-L-mannopyranose (known from US 2014/0275503 A1) (CAS 1181213-14-8); 8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 1253850-56-4), (8-anti)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (CAS 933798-27-7), (8-syn)-8-(2-cyclopropylmethoxy-4-trifluoromethyl-phenoxy)-3-(6-trifluoromethyl-pyridazin-3-yl)-3-aza-bicyclo[3.2.1]octane (known from WO 2007040280 A1, WO 2007040282 A1) (CAS 934001-66-8), N-[3-chloro-1-(3-pyridinyl)-1H-pyrazol-4-yl]-N-ethyl-3-[(3,3,3-trifluoropropyl)thio]-propanamide (known from WO 2015/058021 A1, WO 2015/058028 A1) (CAS 1477919-27-9) and N-[4-(aminothioxomethyl)-2-methyl-6-[(methylamino)carbonyl]phenyl]-3-bromo-1-(3-chloro-2-pyridinyl)-1H-pyrazole-5-carboxamide (known from CN 103265527 A) (CAS 1452877-50-7), 5-(1,3-dioxan-2-yl)-4-[[4-(trifluoromethyl)phenyl]methoxy]-pyrimidine (known from WO 2013/115391 A1) (CAS 1449021-97-9), 3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-methoxy-1-methyl-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2010/066780 A1, WO 2011/151146 A1) (CAS 1229023-34-0), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-1,8-diazaspiro[4.5]decane-2,4-dione (known from WO 2014/187846 A1) (CAS 1638765-58-8), 3-(4-chloro-2,6-dimethylphenyl)-8-methoxy-1-methyl-2-oxo-1, 8-diazaspiro[4.5]dec-3-en-4-yl-carbonic acid ethyl ester (known from WO 2010/066780 A1, WO 2011151146 A1) (CAS 1229023-00-0), N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide (known from DE 3639877 A1, WO 2012029672 A1) (CAS 1363400-41-2), [N(E)]-N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide, (known from WO 2016005276 A1) (CAS 1689566-03-7), [N(Z)]—N-[1-[(6-chloro-3-pyridinyl)methyl]-2(1H)-pyridinylidene]-2,2,2-trifluoro-acetamide, (CAS 1702305-40-5), 3-endo-3-[2-propoxy-4-(trifluoromethyl)phenoxy]-9-[[5-(trifluoromethyl)-2-pyridinyl]oxy]-9-azabicyclo[3.3.1]nonane (known from WO 2011/105506 A1, WO 2016/133011 A1) (CAS 1332838-17-1).

Examples of safeners which could be mixed with the compounds of formula (I) and compositions comprising thereof are, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr

(-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methylcarbamoyl)amino]phenyl}-sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

Examples of herbicides which could be mixed with the compounds of formula (I) and compositions comprising thereof are:

Acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, allidochlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidochlor, amidosulfuron, 4-amino-3-chloro-6-(4-chloro-2-fluoro-3-methylphenyl)-5-fluoropyridine-2-carboxylic acid, aminocyclopyrachlor, aminocyclopyrachlor-potassium, aminocyclopyrachlor-methyl, aminopyralid, amitrole, ammoniumsulfamate, anilofos, asulam, atrazine, azafenidin, azimsulfuron, beflubutamid, benazolin, benazolin-ethyl, benfluralin, benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone, benzobicyclon, benzofenap, bicyclopyron, bifenox, bilanafos, bilanafos-sodium, bispyribac, bispyribac-sodium, bromacil, bromobutide, bromofenoxim, bromoxynil, bromoxynil-butyrate, -potassium, -heptanoate, and -octanoate, busoxinone, butachlor, butafenacil, butamifos, butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide, carfentrazone, carfentrazone-ethyl, chloramben, chlorbromuron, chlorfenac, chlorfenac-sodium, chlorfenprop, chlorflurenol, chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl, chlorophthalim, chlorotoluron, chlorthal-dimethyl, chlorsulfuron, cinidon, cinidon-ethyl, cinmethylin, cinosulfuron, clacyfos, clethodim, clodinafop, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam, cloransulam-methyl, cumyluron, cyanamide, cyanazine, cycloate, cyclopyrimorate, cyclosulfamuron, cycloxydim, cyhalofop, cyhalofop-butyl, cyprazine, 2,4-D, 2,4-D-butotyl, -butyl, -dimethylammonium, -diolamin, -ethyl, -2-ethylhexyl, -isobutyl, -isooctyl, -isopropylammonium, -potassium, -triisopropanolammonium, and -trolamine, 2,4-DB, 2,4-DB-butyl, -dimethylammonium, -isooctyl, -potassium, and -sodium, daimuron (dymron), dalapon, dazomet, n-decanol, desmedipham, detosyl-pyrazolate (DTP), dicamba, dichlobenil, 2-(2,4-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, 2-(2,5-dichlorobenzyl)-4,4-dimethyl-1,2-oxazolidin-3-one, dichlorprop, dichlorprop-P, diclofop, diclofop-methyl, diclofop-P-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimetrasulfuron, dinitramine, dinoterb, diphenamid, diquat, diquat-dibromid, dithiopyr, diuron, DNOC, endothal, EPTC, esprocarb, ethalfluralin, ethametsulfuron, etha-metsulfuron-methyl, ethiozin, ethofumesate, ethoxyfen, ethoxyfen-ethyl, ethoxysulfuron, etobenzanid, F-9600, F-5231, i.e. N-{2-chloro-4-fluoro-5-[4-(3-fluoropropyl)-5-oxo-4,5-dihydro-1H-tetrazol-1-yl]phenyl}ethanesulfonamide, F-7967, i. e. 3-[7-chloro-5-fluoro-2-(trifluoromethyl)-1H-benzimidazol-4-yl]-1-methyl-6-(trifluoromethyl)pyrimidine-2,4(1H,3H)-dione, fenoxaprop, fenoxaprop-P, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fenoxasulfone, fenquinotrione, fentrazamide, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-P, fluazifop-butyl, fluazifop-P-butyl, flucarbazone, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flufenpyr-ethyl, flumetsulam, flumiclorac, flumiclorac-pentyl, flumioxazin, fluometuron, flurenol, flurenol-butyl, -dimethylammonium and -methyl, fluoroglycofen, fluoroglycofen-ethyl, flupropanate, flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone, flurochloridone, fluroxypyr, fluroxypyr-meptyl, flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium, foramsulfuron, fosamine, glufosinate, glufosinate-ammonium, glufosinate-P-sodium, glufosinate-P-ammonium, glufosinate-P-sodium, glyphosate, glyphosate-ammonium, -isopropylammonium, -diammonium, -dimethylammonium, -potassium, -sodium, and -trimesium, H-9201, i.e. O-(2,4-dimethyl-6-nitrophenyl) O-ethyl isopropylphosphoramidothioate, halauxifen, halauxifen-methyl, halosafen, halosulfuron, halosulfuron-methyl, haloxyfop, haloxyfop-P, haloxyfop-ethoxyethyl, haloxyfop-P-ethoxyethyl, haloxyfop-methyl, haloxyfop-P-methyl, hexazinone, HW-02, i.e. 1-(dimethoxyphosphoryl) ethyl-(2,4-dichlorophenoxy)acetate, imazamethabenz, imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic, imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin, imazaquin-ammonium, imazethapyr, imazethapyr-immonium, imazosulfuron, indanofan, indaziflam, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxynil-octanoate, -potassium and -sodium, ipfencarbazone, isoproturon, isouron, isoxaben, isoxaflutole, karbutilate, KUH-043, i.e. 3-({[5-(difluoromethyl)-1-methyl-3-(trifluoromethyl)-1H-pyrazol-4-yl]methyl}sulfonyl)-5,5-dimethyl-4,5-dihydro-1,2-oxazole, ketospiradox, lactofen, lenacil, linuron, MCPA, MCPA-butotyl, -dimethylammonium, -2-ethylhexyl, -isopropylammonium, -potassium, and -sodium, MCPB, MCPB-methyl, -ethyl and -sodium, mecoprop, mecoprop-sodium, and -butotyl, mecoprop-P, mecoprop-P-butotyl, -dimethylammonium, -2-ethylhexyl, and -potassium, mefenacet, mefluidide, mesosulfuron, mesosulfuron-methyl, mesotrione, methabenzthiazuron, metam, metamifop, metamitron, metazachlor, metazosulfuron, methabenzthiazuron, methiopyrsulfuron, methiozolin, methyl isothiocyanate, metobromuron, metolachlor, S-metolachlor, metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl, molinat, monolinuron, monosulfuron, monosulfuron-ester, MT-5950, i.e. N-(3-chloro-4-isopropylphenyl)-2-methylpentan amide, NGGC-011, napropamide, NC-310, i.e. [5-(benzyloxy)-1-methyl-1H-pyrazol-4-yl](2,4-dichlorophenyl)methanone, neburon, nicosulfuron, nonanoic acid (pelargonic acid), norflurazon, oleic acid (fatty acids), orbencarb, orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefon, oxyfluorfen, paraquat, paraquat dichloride, pebulate, pendimethalin, penoxsulam, pentachlorphenol, pentoxazone, pethoxamid, petroleum oils, phenmedipham, picloram, picolinafen, pinoxaden, piperophos, pretilachlor, primisulfuron, primisulfuron-methyl, prodiamine, profoxydim, prometon, prometryn, propachlor, propanil, propaquizafop, propazine, propham, propisochlor, propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide, prosulfocarb, prosulfuron, pyraclonil, pyraflufen, pyraflufen-ethyl, pyrasulfotole, pyrazolynate (pyrazolate), pyrazosulfuron, pyrazosulfuron-ethyl, pyrazoxyfen, pyribambenz, pyribambenz-isopropyl, pyribambenz-propyl, pyribenzoxim, pyributicarb, pyridafol, pyridate, pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac, pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac, quinoclamine, quizalofop, quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, saflufenacil, sethoxydim, siduron, simazine, simetryn, SL-261, sulcotrion, sulfentrazone, sulfometuron, sulfometuron-methyl, sulfosulfuron, SYN-523, SYP-249, i.e. 1-ethoxy-3-methyl-1-oxobut-3-en-2-yl 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate, SYP-300, i.e. 1-[7-fluoro-3-oxo-4-(prop-2-yn-1-yl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-3-propyl-2-thioxoimidazolidine-4,5-dione, 2,3,6-TBA, TCA (trichloroacetic acid), TCA-sodium, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim, terbacil, terbucarb, terbumeton, terbuthylazin, terbutryn, thenylchlor, thiazopyr, thiencarbazone, thien-carbazone-methyl, thifensulfuron, thifensulfuron-methyl, thiobencarb, tiafenacil, tolpyralate, topramezone, tralkoxydim, triafamone, tri-allate, triasulfuron, triaziflam, tribenuron, tribenuron-methyl, triclopyr, trietazine, trifloxysulfuron, trifloxysulfuron-sodium, trifludimoxazin, trifluralin, triflusulfuron, triflusulfuron-methyl, tritosulfuron, urea sulfate, vernolate, XDE-848, ZJ-0862, i.e. 3,4-dichloro-N-{2-[(4,6-dimethoxypyrimidin-2-yl)oxy]benzyl}aniline, and the following compounds:

Examples for plant growth regulators are:

Acibenzolar, acibenzolar-S-methyl, 5-aminolevulinic acid, ancymidol, 6-benzylaminopurine, Brassinolid, catechine, chlormequat chloride, cloprop, cyclanilide, 3-(cycloprop-1-enyl) propionic acid, daminozide, dazomet, n-decanol, dikegulac, dikegulac-sodium, endothal, endothal-dipotassium, -disodium, and -mono(N,N-dimethylalkylammonium), ethephon, flumetralin, flurenol, flurenol-butyl, flurprimidol, forchlorfenuron, gibberellic acid, inabenfide, indol-3-acetic acid (IAA), 4-indol-3-ylbutyric acid, isoprothiolane, probenazole, jasmonic acid, maleic hydrazide, mepiquat chloride, 1-methyl-cyclopropene, methyl jasmonate, 2-(1-naphthyl)acetamide, 1-naphthylacetic acid, 2-naphthyloxyacetic acid, nitrophenolate-mixture, paclobutrazol, N-(2-phenylethyl)-beta-alanine, N-phenylphthalamic acid, prohexadione, prohexadione-calcium, prohydrojasmone, salicylic acid, strigolactone, tecnazene, thidiazuron, triacontanol, trinexapac, trinexapac-ethyl, tsitodef, uniconazole, uniconazole-P.

Methods and Uses

The compounds of formula (I) and the compositions comprising thereof have potent microbicidal activity. They can be used for controlling unwanted microorganisms, such as unwanted fungi and bacteria. They can be particularly useful in crop protection (they control microorganisms that cause plants diseases) or for protecting materials (e.g. industrial materials, timber, storage goods) as described in more details herein below. More specifically, the compounds of formula (I) and the compositions comprising thereof can be used to protect seeds, germinating seeds, emerged seedlings, plants, plant parts, fruits, harvest goods and/or the soil in which the plants grow from unwanted microorganisms.

Control or controlling as used herein encompasses protective, curative and eradicative treatment of unwanted microorganisms. Unwanted microorganisms may be pathogenic bacteria, pathogenic virus, pathogenic oomycetes or pathogenic fungi, more specifically phytopathogenic bacteria phytopathogenic virus, phytopathogenic oomycetes or phytopathogenic fungi. As detailed herein below, these phytopathogenic microorganisms are the causal agents of a broad spectrum of plants diseases.

More specifically, the compounds of formula (I) and compositions comprising thereof can be used as fungicides. For the purpose of the specification, the term “fungicide” refers to a compound or composition that can be used in crop protection for the control of unwanted fungi, such as Plasmodiophoromycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and/or for the control of Oomycetes, more preferably for the control of Basidiomycetes (causing rust diseases).

The present invention also relates to a method for controlling unwanted microorganisms, such as phytopathogenic fungi, oomycetes and bacteria, comprising the step of applying at least one compound of formula (I) or at least one composition comprising thereof to the microorganisms and/or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).

Typically, when the compound and the composition of the invention are used in curative or protective methods for controlling phytopathogenic fungi and/or phytopathogenic oomycetes, an effective and plant-compatible amount thereof is applied to the plants, plant parts, fruits, seeds or to the soil or substrates in which the plants grow. Suitable substrates that may be used for cultivating plants include inorganic based substrates, such as mineral wool, in particular stone wool, perlite, sand or gravel; organic substrates, such as peat, pine bark or sawdust; and petroleum based substrates such as polymeric foams or plastic beads. Effective and plant-compatible amount means an amount that is sufficient to control or destroy the fungi present or liable to appear on the cropland and that does not entail any appreciable symptom of phytotoxicity for said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the crop growth stage, the climatic conditions and the respective compound or composition of the invention used. This amount can be determined by systematic field trials that are within the capabilities of a person skilled in the art.

Plants and Plant Parts

The compounds of formula (I) and compositions comprising thereof may be applied to any plants or plant parts.

Plants mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the genetically modified plants (GMO or transgenic plants) and the plant cultivars which are protectable and non-protectable by plant breeders' rights.

Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoot, leaf, flower and root, examples of which include leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

Plants which may be treated in accordance with the methods of the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp. (for example pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (for example banana trees and plantations), Rubiaceae sp. (for example coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example lemons, oranges and grapefruit); Solanaceae sp. (for example tomatoes), Liliaceae sp., Asteraceae sp. (for example lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example leek, onion), Papilionaceae sp. (for example peas); major crop plants, such as Gramineae sp. (for example maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (for example sunflower), Brassicaceae sp. (for example white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example bean, peanuts), Papilionaceae sp. (for example soya bean), Solanaceae sp. (for example potatoes), Chenopodiaceae sp. (for example sugar beet, fodder beet, swiss chard, beetroot); useful plants and ornamental plants for gardens and wooded areas; and genetically modified varieties of each of these plants.

In some preferred embodiments, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and also parts thereof, are treated in accordance with the methods of the invention.

In some other preferred embodiments, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated in accordance with the methods of the invention. More preferably, plants of the plant cultivars which are commercially available or are in use are treated in accordance with the invention. Plant cultivars are understood to mean plants which have new properties (“traits”) and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.

The methods according to the invention can be used in the treatment of genetically modified organisms (GMOs), e.g. plants or seeds. Genetically modified plants (or transgenic plants) are plants of which a heterologous gene has been stably integrated into genome. The expression “heterologous gene” essentially means a gene which is provided or assembled outside the plant and when introduced in the nuclear, chloroplastic or mitochondrial genome gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by downregulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference—RNAi—technology or microRNA—miRNA—technology). A heterologous gene that is located in the genome is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

Plants and plant cultivars which can be treated by the above disclosed methods include all plants which have genetic material which impart particularly advantageous, useful traits to these plants (whether obtained by breeding and/or biotechnological means).

Plants and plant cultivars which can be treated by the above disclosed methods include plants and plant cultivars which are resistant against one or more biotic stresses, i.e. said plants show a better defense against animal and microbial pests, such as against nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars which can be treated by the above disclosed methods include those plants which are resistant to one or more abiotic stresses. Abiotic stress conditions may include, for example, drought, cold temperature exposure, heat exposure, osmotic stress, flooding, increased soil salinity, increased mineral exposure, ozone exposure, high light exposure, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars which can be treated by the above disclosed methods include those plants characterized by enhanced yield characteristics. Increased yield in said plants can be the result of, for example, improved plant physiology, growth and development, such as water use efficiency, water retention efficiency, improved nitrogen use, enhanced carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. Yield can furthermore be affected by improved plant architecture (under stress and non-stress conditions), including but not limited to, early flowering, flowering control for hybrid seed production, seedling vigor, plant size, internode number and distance, root growth, seed size, fruit size, pod size, pod or ear number, seed number per pod or ear, seed mass, enhanced seed filling, reduced seed dispersal, reduced pod dehiscence and lodging resistance. Further yield traits include seed composition, such as carbohydrate content and composition for example cotton or starch, protein content, oil content and composition, nutritional value, reduction in anti-nutritional compounds, improved processability and better storage stability.

Plants and plant cultivars which can be treated by the above disclosed methods include plants and plant cultivars which are hybrid plants that already express the characteristic of heterosis or hybrid vigor which results in generally higher yield, vigor, health and resistance towards biotic and abiotic stresses. Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars which are herbicide-tolerant plants, i.e. plants made tolerant to one or more given herbicides. Such plants can be obtained either by genetic transformation, or by selection of plants containing a mutation imparting such herbicide tolerance.

Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars which are insect-resistant transgenic plants, i.e. plants made resistant to attack by certain target insects. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such insect resistance.

Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars which are tolerant to abiotic stresses. Such plants can be obtained by genetic transformation, or by selection of plants containing a mutation imparting such stress resistance.

Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars which show altered quantity, quality and/or storage-stability of the harvested product and/or altered properties of specific ingredients of the harvested product.

Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars, such as cotton plants, with altered fiber characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered fiber characteristics.

Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars, such as oilseed rape or related Brassica plants, with altered oil profile characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered oil profile characteristics.

Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars, such as oilseed rape or related Brassica plants, with altered seed shattering characteristics. Such plants can be obtained by genetic transformation, or by selection of plants contain a mutation imparting such altered seed shattering characteristics and include plants such as oilseed rape plants with delayed or reduced seed shattering.

Plants and plant cultivars (obtained by plant biotechnology methods such as genetic engineering) which can be treated by the above disclosed methods include plants and plant cultivars, such as Tobacco plants, with altered post-translational protein modification patterns.

Pathogens and Diseases

The methods disclosed above can be used to control microorganisms, in particular phytopathogenic microorganisms such as phytopathogenic fungi, causing diseases, such as:

diseases caused by powdery mildew pathogens, such as Blumeria species (e.g. Blumeria graminis), Podosphaera species (e.g. Podosphaera leucotricha), Sphaerotheca species (e.g. Sphaerotheca fuliginea), Uncinula species (e.g. Uncinula necator);

diseases caused by rust disease pathogens, such as Gymnosporangium species (e.g. Gymnosporangium sabinae), Hemileia species (e.g. Hemileia vastatrix), Phakopsora species (e.g. Phakopsora pachyrhizi or Phakopsora meibomiae), Puccinia species (e.g. Puccinia recondita, Puccinia graminis or Puccinia striiformis), Uromyces species (e.g. Uromyces appendiculatus);

diseases caused by pathogens from the group of the Oomycetes, such as Albugo species (e.g. Albugo candida), Bremia species (e.g. Bremia lactucae), Peronospora species (e.g. Peronospora pisi or P. brassicae), Phytophthora species (e.g. Phytophthora infestans), Plasmopara species (e.g. Plasmopara viticola), Pseudoperonospora species (e.g. Pseudoperonospora humuli or Pseudoperonospora cubensis), Pythium species (e.g. Pythium ultimum);

leaf blotch diseases and leaf wilt diseases caused, for example, by Alternaria species (e.g. Alternaria solani), Cercospora species (e.g. Cercospora beticola), Cladiosporium species (e.g. Cladiosporium cucumerinum), Cochliobolus species (e.g. Cochliobolus sativus (conidial form: Drechslera, syn: Helminthosporium) or Cochliobolus miyabeanus), Colletotrichum species (e.g. Colletotrichum lindemuthanium), Cycloconium species (e.g. Cycloconium oleaginum), Diaporthe species (e.g. Diaporthe citri), Elsinoe species (e.g. Elsinoe fawcettii), Gloeosporium species (e.g. Gloeosporium laeticolor), Glomerella species (e.g. Glomerella cingulate), Guignardia species (e.g. Guignardia bidwelli), Leptosphaeria species (e.g. Leptosphaeria maculans), Magnaporthe species (e.g. Magnaporthe grisea), Microdochium species (e.g. Microdochium nivale), Mycosphaerella species (e.g. Mycosphaerella graminicola, Mycosphaerella arachidicola or Mycosphaerella fijiensis), Phaeosphaeria species (e.g. Phaeosphaeria nodorum), Pyrenophora species (e.g. Pyrenophora teres or Pyrenophora tritici repentis), Ramularia species (e.g. Ramularia collo-cygni or Ramularia areola), Rhynchosporium species (e.g. Rhynchosporium secalis), Septoria species (e.g. Septoria apii or Septoria lycopersici), Stagonospora species (e.g. Stagonospora nodorum), Typhula species (e.g. Typhula incarnate), Venturia species (e.g. Venturia inaequalis),

root and stem diseases caused, for example, by Corticium species (e.g. Corticium graminearum), Fusarium species (e.g. Fusarium oxysporum), Gaeumannomyces species, (e.g. Gaeumannomyces graminis), Plasmodiophora species, (e.g. Plasmodiophora brassicae), Rhizoctonia species, (e.g. Rhizoctonia solani), Sarocladium species, (e.g. Sarocladium oryzae), Sclerotium species, (e.g. Sclerotium oryzae), Tapesia species, (e.g. Tapesia acuformis), Thielaviopsis species, (e.g. Thielaviopsis basicola);

ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, (e.g. Alternaria spp.), Aspergillus species (e.g. Aspergillus flavus), Cladosporium species (e.g. Cladosporium cladosporioides, Claviceps species (e.g. Claviceps purpurea), Fusarium species, (e.g. Fusarium culmorum), Gibberella species (e.g. Gibberella zeae), Monographella species, (e.g. Monographella nivalis), Stagnospora species, (e.g. Stagnospora nodorum);

diseases caused by smut fungi, for example Sphacelotheca species (e.g. Sphacelotheca reiliana), Tilletia species (e.g. Tilletia caries or Tilletia controversa), Urocystis species (e.g. Urocystis occulta), Ustilago species (e.g. Ustilago nuda);

fruit rot caused, for example, by Aspergillus species (e.g. Aspergillus flavus), Botrytis species (e.g. Botrytis cinerea), Penicillium species (e.g. Penicillium expansum or Penicillium purpurogenum), Rhizopus species (e.g. Rhizopus stolonifer), Sclerotinia species (e.g. Sclerotinia sclerotiorum), Verticilium species (e.g. Verticilium alboatrum);

seed- and soil-borne rot and wilt diseases, and also diseases of seedlings, caused, for example, by Alternaria species (e.g. Alternaria brassicicola), Aphanomyces species (e.g. Aphanomyces euteiches), Ascochyta species (e.g. Ascochyta lentis), Aspergillus species (e.g. Aspergillus flavus), Cladosporium species (e.g. Cladosporium herbarum), Cochliobolus species (e.g. Cochliobolus sativus (conidial form: Drechslera, Bipolaris Syn: Helminthosporium)), Colletotrichum species (e.g. Colletotrichum coccodes), Fusarium species (e.g. Fusarium culmorum), Gibberella species (e.g. Gibberella zeae), Macrophomina species (e.g. Macrophomina phaseolina), Microdochium species (e.g. Microdochium nivale), Monographella species (e.g. Monographella nivalis), Penicillium species (e.g. Penicillium expansum), Phoma species (e.g. Phoma lingam), Phomopsis species (e.g. Phomopsis sojae), Phytophthora species (e.g. Phytophthora cactorum), Pyrenophora species (e.g. Pyrenophora graminea), Pyricularia species (e.g. Pyricularia oryzae), Pythium species (e.g. Pythium ultimum), Rhizoctonia species (e.g. Rhizoctonia solani), Rhizopus species (e.g. Rhizopus oryzae), Sclerotium species (e.g. Sclerotium rolfsii), Septoria species (e.g. Septoria nodorum), Typhula species (e.g. Typhula incarnate), Verticillium species (e.g. Verticillium dahlia);

cancers, galls and witches' broom caused, for example, by Nectria species (e.g. Nectria galligena); wilt diseases caused, for example, by Monilinia species (e.g. Monilinia laxa);

deformations of leaves, flowers and fruits caused, for example, by Exobasidium species (e.g. Exobasidium vexans), Taphrina species (e.g. Taphrina deformans);

degenerative diseases in woody plants, caused, for example, by Esca species (e.g. Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea), Ganoderma species (e.g. Ganoderma boninense);

diseases of flowers and seeds caused, for example, by Botrytis species (e.g. Botrytis cinerea); diseases of plant tubers caused, for example, by Rhizoctonia species (e.g. Rhizoctonia solani), Helminthosporium species (e.g. Helminthosporium solani);

diseases caused by bacterial pathogens, for example Xanthomonas species (e.g. Xanthomonas campestris pv. Oryzae), Pseudomonas species (e.g. Pseudomonas syringae pv. Lachrymans), Erwinia species (e.g. Erwinia amylovora).

Seed Treatment

The method for controlling unwanted microorganisms may be used to protect seeds from phytopathogenic microorganisms, such as fungi.

The term “seed(s)” as used herein include dormant seed, primed seed, pregerminated seed and seed with emerged roots and leaves.

Thus, the present invention also relates to a method for protecting seeds and/or crops from unwanted microorganisms, such as bacteria or fungi, which comprises the step of treating the seeds with one or more compounds of formula (I) or a composition comprising thereof. The treatment of seeds with the compound(s) of formula (I) or a composition comprising thereof not only protects the seeds from phytopathogenic microorganisms, but also the germinating plants, the emerged seedlings and the plants after emergence.

The seeds treatment may be performed prior to sowing, at the time of sowing or shortly thereafter. When the seeds treatment is performed prior to sowing (e.g. so-called on-seed applications), the seeds treatment may be performed as follows: the seeds may be placed into a mixer with a desired amount of compound(s) of formula (I) or a composition comprising thereof (either as such or after dilution), the seeds and the compound(s) of formula (I) or the composition comprising thereof are mixed until a homogeneous distribution on seeds is achieved. If appropriate, the seeds may then be dried.

The invention also relates to seeds treated with one or more compounds of formula (I) or a composition comprising thereof. As said before, the use of treated seeds allows not only protecting the seeds before and after sowing from unwanted microorganisms, such as phytopathogenic fungi, but also allows protecting the germinating plants and young seedlings emerging from said treated seeds. A large part of the damage to crop plants caused by harmful organisms is triggered by the infection of the seeds before sowing or after germination of the plant. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive, and even small damage may result in the death of the plant.

Therefore, the present invention also relates to a method for protecting seeds, germinating plants and emerged seedlings, more generally to a method for protecting crop from phytopathogenic microorganisms, which comprises the step of using seeds treated by one or more compounds of formula (I) or a composition comprising thereof.

Preferably, the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment. In general, seeds can be treated at any time between harvest and shortly after sowing. It is customary to use seeds which have been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seeds which have been harvested, cleaned and dried down to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds which, after drying, for example, have been treated with water and then dried again, or seeds just after priming, or seeds stored in primed conditions or pregerminated seeds, or seeds sown on nursery trays, tapes or paper.

The amount of compound(s) of formula (I) or composition comprising thereof applied to the seed is typically such that the germination of the seed is not impaired, or that the resulting plant is not damaged. This must be ensured particularly in case the active ingredients would exhibit phytotoxic effects at certain application rates. The intrinsic phenotypes of transgenic plants should also be taken into consideration when determining the amount of compound(s) of formula (I) or composition comprising thereof to be applied to the seed in order to achieve optimum seed and germinating plant protection with a minimum amount of compound(s) of formula (I) or composition comprising thereof being employed.

As indicated above, the compounds of the formula (I) can be applied, as such, directly to the seeds, i.e. without the use of any other components and without having been diluted, or a composition comprising the compounds of formula (I) can be applied. Preferably, the compositions are applied to the seed in any suitable form. Examples of suitable formulations include solutions, emulsions, suspensions, powders, foams, slurries or combined with other coating compositions for seed, such as film forming materials, pelleting materials, fine iron or other metal powders, granules, coating material for inactivated seeds, and also ULV formulations. The formulations may be ready-to-use formulations or may be concentrates that need to be diluted prior to use.

These formulations are prepared in a known manner, for instance by mixing the active ingredient or mixture thereof with customary additives, for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.

These formulations are prepared in a known manner, by mixing the active ingredients or active ingredient combinations with customary additives, for example customary extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins, and also water.

Useful dyes which may be present in the seed dressing formulations are all dyes which are customary for such purposes. It is possible to use either pigments, which are sparingly soluble in water, or dyes, which are soluble in water. Examples include the dyes known by the names Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1. Useful wetting agents which may be present in the seed dressing formulations are all substances which promote wetting and which are conventionally used for the formulation of active agrochemical ingredients. Usable with preference are alkylnaphthalenesulfonates, such as diisopropyl- or diisobutylnaphthalenesulfonates. Useful dispersants and/or emulsifiers which may be present in the seed dressing formulations are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Usable with preference are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Useful nonionic dispersants include especially ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ether, and the phosphated or sulfated derivatives thereof. Suitable anionic dispersants are especially lignosulfonates, polyacrylic acid salts and arylsulfonate/formaldehyde condensates. Antifoams which may be present in the seed dressing formulations are all foam-inhibiting substances conventionally used for the formulation of active agrochemical ingredients. Silicone antifoams and magnesium stearate can be used with preference. Preservatives which may be present in the seed dressing formulations are all substances usable for such purposes in agrochemical compositions. Examples include dichlorophene and benzyl alcohol hemiformal. Secondary thickeners which may be present in the seed dressing formulations are all substances usable for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica. Adhesives which may be present in the seed dressing formulations are all customary binders usable in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The compounds of the formula (I) and the compositions comprising thereof are suitable for protecting seeds of any plant variety which is used in agriculture, in greenhouses, in forests or in horticulture. More particularly, the seed is that of cereals (such as wheat, barley, rye, millet, triticale, and oats), oilseed rape, maize, cotton, soybean, rice, potatoes, sunflower, beans, coffee, peas, beet (e.g. sugar beet and fodder beet), peanut, vegetables (such as tomato, cucumber, onions and lettuce), lawns and ornamental plants. Of particular significance is the treatment of the seed of wheat, soybean, oilseed rape, maize and rice.

The compounds of formula (I) or the compositions comprising thereof can be used for treating transgenic seeds, in particular seeds of plants capable of expressing a protein which acts against pests, herbicidal damage or abiotic stress, thereby increasing the protective effect. Synergistic effects may also occur in interaction with the substances formed by expression.

Nematodes

In the present context, the term “nematodes” comprises all species of the phylum Nematoda and here in particular species acting as parasites on plants or fungi (for example species of the order Aphelenchida, Meloidogyne, Tylenchida and others) or else on humans and animals (for example species of the orders Trichinellida, Tylenchida, Rhabditina and Spirurida) and causing damage in or on these living organisms, and also other parasitic helminths.

A nematicide in crop protection, as described herein, is capable of controlling nematodes.

The term “controlling nematodes” means killing the nematodes or preventing or impeding their development or their growth or preventing or impeding their penetration into or their sucking on plant tissue. Here, the efficacy of the compounds is determined by comparing mortalities, gall formation, cyst formation, nematode density per volume of soil, nematode density per root, number of nematode eggs per soil volume, mobility of the nematodes between a plant or plant part treated with the compound of the formula (I) or the treated soil and an untreated plant or plant part or the untreated soil (100%). Preferably, the reduction achieved is 25-50% in comparison to an untreated plant, plant part or the untreated soil, particularly preferably 51-79% and very particularly preferably the complete kill or the complete prevention of development and growth of the nematodes by a reduction of 80 to 100%. The control of nematodes as described herein also comprises the control of proliferation of the nematodes (development of cysts and/or eggs). Compounds of the formula (I) can also be used to keep the plants or animals healthy, and they can be employed curatively, preventatively or systemically for the control of nematodes. The person skilled in the art knows methods for determining mortalities, gall formation, cyst formation, nematode density per volume of soil, nematode density per root, number of nematode eggs per volume of soil, mobility of the nematodes.

The use of a compound of the formula (I) may keep the plant healthy and also comprises a reduction of the damage caused by nematodes and an increase of the harvest yield.

In the present context, the term “nematodes” refers to plant nematodes which comprise all nematodes which damage plants. Plant nematodes comprise phytoparasitic nematodes and soil-borne nematodes. The phytoparasitic nematodes include ectoparasites such as Xiphinema spp., Longidorus spp. and Trichodorus spp.; semiparasites such as Tylenchulus spp.; migratory endoparasites such as Pratylenchus spp., Radopholus spp. and Scutellonema spp.; non-migratory parasites such as Heterodera spp., Globodera spp. and Meloidogyne spp., and also stem and leaf endoparasites such as Ditylenchus spp., Aphelenchoides spp. and Hirschmaniella spp. Particularly damaging root-parasitic soil nematodes are, for example, cyst-forming nematodes of the genera Heterodera or Globodera, and/or root gall nematodes of the genus Meloidogyne. Damaging species of these genera are, for example, Meloidogyne incognita, Heterodera glycines (soya bean cyst nematode), Globodera pallida and Globodera rostochiensis (yellow potato cyst nematode), these species being controlled effectively by the compounds described in the present text. However, the use of the compounds described in the present text is by no means restricted to these genera or species, but also extends in the same manner to other nematodes.

The plant nematodes include, for example, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria, and the stem and leaf endoparasites Aphelenchoides spp., Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus und Bursaphelenchus spp., Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (=Mesocriconema xenoplax) and Criconemella spp., Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum and Criconemoides spp., Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus and also the stem and leaf endoparasites Ditylenchus spp., Dolichodorus heterocephalus, Globodera pallida (=Heterodera pallida), Globodera rostochiensis (yellow potato cyst nematode), Globodera solanacearum, Globodera tabacum, Globodera virginia and the non-migratory cyst-forming parasites Globodera spp., Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus erythrine, Helicotylenchus multicinctus, Helicotylenchus nannus, Helicotylenchus pseudorobustus and Helicotylenchus spp., Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, Heterodera cruciferae, Heterodera glycines (soya bean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae and the non-migratory cyst-forming parasites Heterodera spp., Hirschmaniella gracilis, Hirschmaniella oryzae, Hirschmaniella spinicaudata and the stem and leaf endoparasites Hirschmaniella spp., Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus columbus, Hoplolaimus galeatus, Hoplolaimus indicus, Hoplolaimus magnistylus, Hoplolaimus pararobustus, Longidorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, Longidorus vineacola and the ectoparasites Longidorus spp., Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua, Meloidogyne fallax, Meloidogyne graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, Meloidogyne paranaensis, Meloidogyne thamesi and the non-migratory parasites Meloidogyne spp., Meloinema spp., Nacobbus aberrans, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor, Paratrichodorus nanus, Paratrichodorus porosus, Paratrichodorus teres and Paratrichodorus spp., Paratylenchus hamatus, Paratylenchus minutus, Paratylenchus projectus and Paratylenchus spp., Pratylenchus agilis, Pratylenchus alleni, Pratylenchus andinus, Pratylenchus brachyurus, Pratylenchus cerealis, Pratylenchus coffeae, Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchus giibbicaudatus, Pratylenchus goodeyi, Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae and the migratory endoparasites Pratylenchus spp., Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis, Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, the migratory endoparasites Radopholus spp., Rotylenchulus borealis, Rotylenchulus parvus, Rotylenchulus reniformis and Rotylenchulus spp., Rotylenchus laurentinus, Rotylenchus macrodoratus, Rotylenchus robustus, Rotylenchus uniformis and Rotylenchus spp., Scutellonema brachyurum, Scutellonema bradys, Scutellonema clathricaudatum and the migratory endoparasites Scutellonema spp., Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus and the ectoparasites Trichodorus spp., Tylenchorhynchus agri, Tylenchorhynchus brassicae, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris and Tylenchorhynchus spp., Tylenchulus semipenetrans and the semiparasites Tylenchulus spp., Xiphinema americanum, Xiphinema brevicolle, Xiphinema dimorphicaudatum, Xiphinema index and the ectoparasites Xiphinema spp.

Nematodes for the control of which a compound of the formula (I) may be used include nematodes of the genus Meloidogyne such as the Southern root-knot nematode (Meloidogyne incognita), the Javanese root-knot nematode (Meloidogyne javanica), the Northern root-knot nematode (Meloidogyne hapla) and the peanut root-knot nematode (Meloidogyne arenaria); nematodes of the genus Ditylenchus such as the potato rot nematode (Ditylenchus destructor) and stem and bulb eelworm (Ditylenchus dipsaci); nematodes of the genus Pratylenchus such as the cob root-lesion nematode (Pratylenchus penetrans), the chrysanthemum root-lesion nematode (Pratylenchus fallax), the coffee root nematode (Pratylenchus coffeae), the tea root nematode (Pratylenchus loosi) and the walnut root-lesion nematode (Pratylenchus vulnus); nematodes of the genus Globodera such as the yellow potato cyst nematode (Globodera rostochiensis) and the white potato cyst nematode (Globodera pallida); nematodes of the genus Heterodera such as the soya bean cyst nematode (Heterodera glycines) and beet cyst eelworm (Heterodera schachtii); nematodes of the genus Aphelenchoides such as the rice white-tip nematode (Aphelenchoides besseyi), the chrysanthemum nematode (Aphelenchoides ritzemabosi) and the strawberry nematode (Aphelenchoides fragariae); nematodes of the genus Aphelenchus such as the fungivorous nematode (Aphelenchus avenae); nematodes of the genus Radopholus, such as the burrowing nematode (Radopholus similis); nematodes of the genus Tylenchulus such as the citrus root nematode (Tylenchulus semipenetrans); nematodes of the genus Rotylenchulus such as the reniform nematode (Rotylenchulus reniformis); tree-dwelling nematodes such as the pine wood nematode (Bursaphelenchus xylophilus) and the red ring nematode (Bursaphelenchus cocophilus) and the like.

Plants for the protection of which a compound of the formula (I) can be used include plants such as cereals (for example rice, barley, wheat, rye, oats, maize and the like), beans (soya bean, aduki bean, bean, broadbean, peas, peanuts and the like), fruit trees/fruits (apples, citrus species, pears, grapevines, peaches, Japanese apricots, cherries, walnuts, almonds, bananas, strawberries and the like), vegetable species (cabbage, tomato, spinach, broccoli, lettuce, onions, spring onion, pepper and the like), root crops (carrot, potato, sweet potato, radish, lotus root, turnip and the like), plant for industrial raw materials (cotton, hemp, paper mulberry, mitsumata, rape, beet, hops, sugar cane, sugar beet, olive, rubber, palm trees, coffee, tobacco, tea and the like), cucurbits (pumpkin, cucumber, water melon, melon and the like), meadow plants (cocksfoot, sorghum, timothy-grass, clover, alfalfa and the like), lawn grasses (mascarene grass, bentgrass and the like), spice plants etc. (lavender, rosemary, thyme, parsley, pepper, ginger and the like) and flowers (chrysanthemums, rose, orchid and the like).

The compounds of the formula (I) are particularly suitable for controlling coffee nematodes, in particular Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, Helicotylenchus spp. and also Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp., Tylenchorhynchus spp. and Scutellonema spp.

The compounds of the formula (I) are particularly suitable for controlling potato nematodes, in particular Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus penetrans, Pratylenchus coffeae, Ditylenchus dipsaci and of Pratylenchus alleni, Pratylenchus andinus, Pratylenchus cerealis, Pratylenchus crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Pratylenchus thornei, Pratylenchus vulnus, Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Trichodorus similis, Trichodorus sparsus, Paratrichodorus minor, Paratrichodorus allius, Paratrichodorus nanus, Paratrichodorus teres, Meloidogyne arenaria, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita, Meloidogyne chitwoodi, Meloidogyne javanica, Nacobbus aberrans, Globodera rostochiensis, Globodera pallida, Ditylenchus destructor, Radopholus similis, Rotylenchulus reniformis, Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Aphelenchoides fragariae and Meloinema spp.

The compounds of the formula (I) are particularly suitable for controlling tomato nematodes, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Pratylenchus penetrans and also Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus, Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus and Rotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable for controlling cucumber plant nematodes, in particular Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Rotylenchulus reniformis and Pratylenchus thornei.

The compounds of the formula (I) are particularly suitable for controlling cotton nematodes, in particular Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable for controlling maize nematodes, in particular Belonolaimus longicaudatus, Paratrichodorus minor and also Pratylenchus brachyurus, Pratylenchus delattrei, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, (Belonolaimus gracilis), Belonolaimus nortoni, Longidorus breviannulatus, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Meloidogyne graminis, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne naasi, Heterodera avenae, Heterodera oryzae, Heterodera zeae, Punctodera chalcoensis, Ditylenchus dipsaci, Hoplolaimus aegyptii, Hoplolaimus magnistylus, Hoplolaimus galeatus, Hoplolaimus indicus, Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus pseudorobustus, Xiphinema americanum, Dolichodorus heterocephalus, Criconemella ornata, Criconemella onoensis, Radopholus similis, Rotylenchulus borealis, Rotylenchulus parvus, Tylenchorhynchus agri, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchus nudus, Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchus minutus, Hemicycliophora parvana, Aglenchus agricola, Anguina tritici, Aphelenchoides arachidis, Scutellonema brachyurum and Subanguina radiciola.

The compounds of the formula (I) are particularly suitable for controlling soya bean nematodes, in particular Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Pratylenchus scribneri, Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus and also Pratylenchus coffeae, Pratylenchus hexincisus, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus zeae, Pratylenchus vulnus, (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Hoplolaimus columbus, Hoplolaimus galeatus and Rotylenchulus reniformis.

The compounds of the formula (I) are particularly suitable for controlling tobacco nematodes, in particular Meloidogyne incognita, Meloidogyne javanica and also Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thornei, Pratylenchus vulnus, Pratylenchus zeae, Longidorus elongatu, Paratrichodorus lobatus, Trichodorus spp., Meloidogyne arenaria, Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus spp., Helicotylenchus spp., Xiphinema americanum, Criconemella spp., Rotylenchulus reniformis, Tylenchorhynchus claytoni, Paratylenchus spp. and Tetylenchus nicotianae.

The compounds of the formula (I) are particularly suitable for controlling citrus nematodes, in particular Pratylenchus coffeae and also Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus, Paratrichodorus minor, Paratrichodorus porosus, Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp., Hemicriconemoides, Radopholus similis and Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulus semipenetrans.

The compounds of the formula (I) are particularly suitable for controlling banana nematodes, in particular Pratylenchus coffeae, Radopholus similis and also Pratylenchus giibbicaudatus, Pratylenchus loosi, Meloidogyne spp., Helicotylenchus multicinctus, Helicotylenchus dihystera and Rotylenchulus spp.

The compounds of the formula (I) are particularly suitable for controlling pineapple nematodes, in particular Pratylenchus zeae, Pratylenchus pratensis, Pratylenchus brachyurus, Pratylenchus goodeyi, Meloidogyne spp., Rotylenchulus reniformis and also Longidorus elongatus, Longidorus laevicapitatus, Trichodorus primitivus, Trichodorus minor, Heterodera spp., Ditylenchus myceliophagus, Hoplolaimus californicus, Hoplolaimus pararobustus, Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicotylenchus multicinctus, Helicotylenchus erythrine, Xiphinema dimorphicaudatum, Radopholus similis, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Paratylenchus minutus, Scutellonema clathricaudatum, Scutellonema bradys, Psilenchus tumidus, Psilenchus magnidens, Pseudohalenchus minutus, Criconemoides ferniae, Criconemoides onoense and Criconemoides ornatum.

The compounds of the formula (I) are particularly suitable for controlling grapevine nematodes, in particular Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index and also Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus, Pratylenchus brachyurus, Pratylenchus thornei and Tylenchulus semipenetrans.

The compounds of the formula (I) are particularly suitable for controlling nematodes in tree crops—pome fruit, in particular Pratylenchus penetrans and also Pratylenchus vulnus, Longidorus elongatus, Meloidogyne incognita and Meloidogyne hapla.

The compounds of the formula (I) are particularly suitable for controlling nematodes in tree crops—stone fruit, in particular Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax and of Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, Criconemella curvata, Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scutellonema brachyurum and Hoplolaimus galeatus.

The compounds of the formula (I) are particularly suitable for controlling nematodes in tree crops, sugar cane and rice, in particular Trichodorus spp., Criconemella spp. and also Pratylenchus spp., Paratrichodorus spp., Meloidogyne spp., Helicotylenchus spp., Tylenchorhynchus spp., Aphelenchoides spp., Heterodera spp, Xiphinema spp. and Cacopaurus pestis.

Application

The compound of formula (I) can be applied as such, or for example in the form of as ready-to-use solutions, emulsions, water- or oil-based suspensions, powders, wettable powders, pastes, soluble powders, dusts, soluble granules, granules for broadcasting, suspoemulsion concentrates, natural products impregnated with the compound of formula (I), synthetic substances impregnated with the compound of formula (I), fertilizers or microencapsulations in polymeric substances.

Application is accomplished in a customary manner, for example by watering, spraying, atomizing, broadcasting, dusting, foaming, spreading-on and the like. It is also possible to deploy the compound of formula (I) by the ultra-low volume method, via a drip irrigation system or drench application, to apply it in-furrow or to inject it into the soil stem or trunk. It is further possible to apply the compound of formula (I) by means of a wound seal, paint or other wound dressing.

The effective and plant-compatible amount of the compound of formula (I) which is applied to the plants, plant parts, fruits, seeds or soil will depend on various factors, such as the compound/composition employed, the subject of the treatment (plant, plant part, fruit, seed or soil), the type of treatment (dusting, spraying, seed dressing), the purpose of the treatment (curative and protective), the type of microorganisms, the development stage of the microorganisms, the sensitivity of the microorganisms, the crop growth stage and the environmental conditions.

When the compound of formula (I) is used as a fungicide, the application rates can vary within a relatively wide range, depending on the kind of application. For the treatment of plant parts, such as leaves, the application rate may range from 0.1 to 10 000 g/ha, preferably from 10 to 1000 g/ha, more preferably from 50 to 300 g/ha (in the case of application by watering or dripping, it is even possible to reduce the application rate, especially when inert substrates such as rockwool or perlite are used). For the treatment of seeds, the application rate may range from 0.1 to 200 g per 100 kg of seeds, preferably from 1 to 150 g per 100 kg of seeds, more preferably from 2.5 to 25 g per 100 kg of seeds, even more preferably from 2.5 to 12.5 g per 100 kg of seeds. For the treatment of soil, the application rate may range from 0.1 to 10 000 g/ha, preferably from 1 to 5000 g/ha.

These application rates are merely examples and are not intended to limit the scope of the present invention.

Material Protection

The compound and the composition of the invention may also be used in the protection of materials, especially for the protection of industrial materials against attack and destruction by unwanted microorganisms.

In addition, the compound and the composition of the invention may be used as antifouling compositions, alone or in combinations with other active ingredients.

Industrial materials in the present context are understood to mean inanimate materials which have been prepared for use in industry. For example, industrial materials which are to be protected from microbial alteration or destruction may be adhesives, glues, paper, wallpaper and board/cardboard, textiles, carpets, leather, wood, fibers and tissues, paints and plastic articles, cooling lubricants and other materials which can be infected with or destroyed by microorganisms. Parts of production plants and buildings, for example cooling-water circuits, cooling and heating systems and ventilation and air-conditioning units, which may be impaired by the proliferation of microorganisms may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, sizes, paper and card, leather, wood, paints, cooling lubricants and heat transfer fluids, more preferably wood.

The compound and the composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould.

In the case of treatment of wood the compound and the composition of the invention may also be used against fungal diseases liable to grow on or inside timber.

Timber means all types of species of wood, and all types of working of this wood intended for construction, for example solid wood, high-density wood, laminated wood, and plywood. In addition, the compound and the composition of the invention may be used to protect objects which come into contact with saltwater or brackish water, especially hulls, screens, nets, buildings, moorings and signaling systems, from fouling.

The compound and the composition of the invention may also be employed for protecting storage goods. Storage goods are understood to mean natural substances of vegetable or animal origin or processed products thereof which are of natural origin, and for which long-term protection is desired. Storage goods of vegetable origin, for example plants or plant parts, such as stems, leaves, tubers, seeds, fruits, grains, may be protected freshly harvested or after processing by (pre)drying, moistening, comminuting, grinding, pressing or roasting. Storage goods also include timber, both unprocessed, such as construction timber, electricity poles and barriers, or in the form of finished products, such as furniture. Storage goods of animal origin are, for example, hides, leather, furs and hairs. The compound and the composition of the invention may prevent adverse effects, such as rotting, decay, discoloration, decoloration or formation of mould. Microorganisms capable of degrading or altering industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compound and the composition of the invention preferably act against fungi, especially moulds, wood-discoloring and wood-destroying fungi (Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria, such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus, such as Polyporus versicolor; Aureobasidium, such as Aureobasidium pullulans; Sclerophoma, such as Sclerophoma pityophila; Trichoderma, such as Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, such as Escherichia coli; Pseudomonas, such as Pseudomonas aeruginosa; Staphylococcus, such as Staphylococcus aureus, Candida spp. and Saccharomyces spp., such as Saccharomyces cerevisae.

Aspects of the present teaching may be further understood in light of the following examples, which should not be construed as limiting the scope of the present teaching in any way.

EXAMPLES

Synthesis of Compounds of Formula (I)

Preparation example 1: Preparation of S-ethyl 1-{[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarbothioate (Compound I.049) Step 1: Preparation of methyl 1-{[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylate

To a solution of 2.08 g (12.3 mmol) of 2-chloro-1,3-dimethylimidazolidinium chloride dissolved in 12.3 mL of dichloromethane was added to a solution of 2.00 g (9.47 mmol) of 4,5-dichloro-3-methylthiophene-2-carboxylic acid and 7.10 mL (40.7 mmol) of N,N-diisopropylethylamine dissolved in 75 mL of dichloromethane. After 15 min of stirring, 333 mg (2.37 mmol) of methyl 1-aminocyclopropanecarboxylate hydrochloride (1:1) was added and the reaction mixture was stirred at room temperature for 72 hours. Water was added and the resulting reaction mixture was extracted twice with dichloromethane. Combined organic layers were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by a first column chromatography on silica gel (gradient n-heptane/ethyl acetate) than a second column chromatography on silica gel (gradient dichloromethane/ethyl acetate) to yield 2.12 g (98% purity, 71% yield) of title compound as a white solid. Log P=2.75. (M+H)=308.

Step 2: Preparation of 1-{[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid

To a solution of 600 mg (1.94 mmol) of methyl 1-{[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylate in 16 mL of tetrahydrofuran was added dropwise 4.3 mL of a 1 M aqueous potassium hydroxide solution (4.3 mmol). The reaction mixture was stirred at room temperature for 18 hours. The resulting reaction mixture was then carefully acidified to pH 1 with a 1.0 M aqueous hydrochloric acid solution at 0° C. and extracted three times with ethyl acetate. Combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure to yield 557 mg (100% purity, 97% yield) of title compound as a white solid. Log P=2.17. (M+H)=294.

Step 3: Preparation of S-ethyl 1-{[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarbothioate (compound I.049)

Under inert atmosphere, to a solution of 100 mg (0.34 mmol) of 1-{[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}cyclopropanecarboxylic acid in 3.2 mL of dry dichloromethane were added, at room temperature, 178 μL (1.02 mmol) of N,N-diisopropylethylamine followed by 194 mg (0.51 mmol) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate. After 15 min of stirring at room temperature, 32 mg (0.51 mmol) of ethanethiol was added and the reaction mixture was stirred at room temperature for 18 hours. A saturated aqueous sodium bicarbonate solution was added and the resulting reaction mixture was extracted twice with dichloromethane. Combined organic layers were filtered through a silica gel cartridge and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient n-heptane/ethyl acetate) to yield 56 mg (100% purity, 49% yield) of title compound as a white solid. Log P=3.67. (M+H)=338.

Preparation Example 2: Preparation of ethyl 1-({N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]glycyl}amino)cyclopropanecarboxylate (Compound I.024) Step 1: Preparation of N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]glycine

In a first round-bottom flask, to a solution of 300 mg (1.0 mmol) of 4,5-dibromo-3-methylthiophene-2-carboxylic acid in 8 mL of dry dichloromethane, were added, at room temperature, 96 μL (1.1 mmol) of oxalyl chloride and a drop of N,N-dimethylformamide. After 1 h of stirring at room temperature, the reaction mixture was concentrated under reduced pressure and dissolved in 6 mL of dry 1,4-dioxane to afford a solution of acyl chloride. In a second round-bottom flask, to a solution of 150 mg (2.0 mmol) of glycine in 0.9 mL of water, was added 1 mL of a 2 M aqueous sodium hydroxide solution (2.0 mmol). The reaction mixture was stirred at room temperature and then slowly added onto the previously prepared solution of acyl chloride at 0° C. Additional 0.5 mL of a 2 M aqueous sodium hydroxide solution (1.0 mmol) was added to the reaction mixture. The resulting reaction mixture was stirred at room temperature for 18 hours, diluted with water and carefully acidified to pH 1 with a 37% (w/w) aqueous hydrochloric acid solution at 0° C. The resulting precipitate was filtered off, washed with water and dissolved in ethyl acetate. The resulting organic layer was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to yield 233 mg (100% purity, 65% yield) of title compound as a white solid. Log P=2.05. (M+H)=356.

Step 2: Preparation of ethyl 1-({N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]glycyl}amino)cyclopropanecarboxylate (Compound I.024)

In a 50 mL round-bottom flask vial under inert atmosphere, to a solution of 208 mg (0.58 mmol) of N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]glycine and 304 μL (1.74 mmol) of N,N-diisopropylethylamine in 5 mL of dry dichloromethane was added, at room temperature, 144 mg (0.87 mmol) of ethyl 1-aminocyclopropanecarboxylate hydrochloride (1:1) followed by 332 mg (0.87 mmol) of 1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium 3-oxid hexafluorophosphate. The reaction mixture was stirred at room temperature for 18 hours. A saturated aqueous sodium bicarbonate solution was added and the resulting reaction mixture was extracted twice with dichloromethane. Combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient n-heptane/ethyl acetate) to yield 225 mg (100% purity, 82% yield) of title compound as a white solid. Log P=2.55. (M+H)=467.

Preparation Example 3: Preparation of ethyl N-[(4,5-dibromo-3-methyl-2-thienyl)carbonothioyl]valinate (Compound I.023) Step 1: Preparation of ethyl N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]valinate

To a solution of 154 mg (0.50 mmol) of 4,5-dibromo-3-methylthiophene-2-carboxylic acid and 183 mg (1.00 mmol) of DL-valine ethyl ester hydrochloride dissolved in 3 mL of tetrahydrofuran was added 0.21 mL (1.51 mmol) of triethylamine followed by 0.45 mL (0.75 mmol) of a 50% (w/w) propanephosphonic anhydride solution in ethyl acetate. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. Combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient n-heptane/ethyl acetate) to yield 103 mg (95% purity, 45% yield) of title compound as a white solid. Log P=4.32. (M+H)=426.

Step 2: Preparation of ethyl N-[(4,5-dibromo-3-methyl-2-thienyl)carbonothioyl]valinate (Compound I.023)

To a solution of 150 mg (0.35 mmol) of ethyl N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]valinate in 1.5 mL of dichloromethane was added 71 mg (0.17 mmol) of Lawesson reagent. The reaction mixture was stirred at 50° C. for 20 hours. The resulting reaction mixture was diluted with dichloromethane, filtered through a basic Chromabond® Alumina cartridge and concentrated under reduced pressure. The residue was purified by preparative high performance liquid chromatography (gradient acetonitrile/aqueous solution of formic acid (1%)) to yield 106 mg (100% purity, 68% yield) of title compound as a yellow solid. Log P=5.22. (M+H)=442.

Preparation Example 4: Preparation of N-[(4,5-dibromo-3-methyl-2-thienyl)carbonothioyl]valine (Compound I.031)

To a solution of 203 mg (0.47 mmol) of ethyl N-[(4,5-dibromo-3-methyl-2-thienyl)carbonothioyl]valinate (compound I.023) in 8 mL of tetrahydrofuran was added dropwise 2.56 mL of a 1 M aqueous potassium hydroxide solution (2.56 mmol). The reaction mixture was stirred at room temperature for 18 hours. A solution of lithium hydroxide 33 mg (1.39 mmol) in 2 mL of water was added and the resulting reaction mixture was stirred at room temperature for 6 hours. Additional lithium hydroxide 28 mg (1.15 mmol) was added and the resulting reaction mixture was further stirred at room temperature for 48 hours. The resulting reaction mixture was then carefully acidified to pH 1 with a 1.0 M aqueous hydrochloric acid solution at 0° C. and extracted three times with ethyl acetate. Combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure to yield 479 mg (98% purity, 97% yield) of title compound as a yellow solid. Log P=3.72. (M−H)=412.

Preparation Example 5: Preparation of cyclopropyl{[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]amino}acetic acid (Compound I.080)

In a first round-bottom flask, to a solution of 120 mg (0.4 mmol) of 4,5-dibromo-3-methylthiophene-2-carboxylic acid in 3 mL of dry dichloromethane, were added, at room temperature, 38 μL (0.44 mmol) of oxalyl chloride and a drop of N,N-dimethylformamide. After 45 minutes of stirring at room temperature, the reaction mixture was concentrated under reduced pressure and dissolved in 2 mL of dry 1,4-dioxane to afford a solution of acyl chloride. In a second round-bottom flask, to a solution of 121 mg (0.8 mmol) of amino(cyclopropyl)acetic acid hydrochloride (1:1) in 0.6 mL of water, was added 1.6 mL of a 1 M aqueous sodium hydroxide solution (1.6 mmol). The reaction mixture was stirred at room temperature for 30 minutes and then slowly added onto the previously prepared solution of acyl chloride at 0° C. The resulting reaction mixture was stirred at room temperature for 24 hours, diluted with water and carefully acidified to pH 1 with a 1.0 M aqueous hydrochloric acid solution at 0° C. and extracted with ethyl acetate. Combined organic layers were filtered through a Chem Elut™ cartridge and concentrated under reduced pressure. The residue was purified by preparative high performance liquid to yield 60 mg (100% purity, 38% yield) of title compound as a white solid. Log P=2.67. (M+H)=396.

Preparation Example 6: Preparation of methyl cyclopropyl{[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}acetate (Compound I.081)

To a solution of 180 mg (1.06 mmol) of 2-chloro-1,3-dimethylimidazolidinium chloride dissolved in 3 mL of dichloromethane was added to a solution of 150 mg (0.71 mmol) of 4,5-dichloro-3-methylthiophene-2-carboxylic acid, 532 μL (3.05 mmol) of N,N-diisopropylethylamine and 176 mg (1.06 mmol) of methyl amino(cyclopropyl)acetate hydrochloride (1:1) in 3 mL of dichloromethane. The reaction mixture was stirred at room temperature for 18 hours. Water was added and the resulting reaction mixture was extracted twice with dichloromethane. Combined organic layers were dried over anhydrous magnesium sulfate, filtrated and concentrated under reduced pressure. The residue was dissolved in dichloromethane, filtered through a silica gel cartridge and concentrated under reduced pressure. The residue was purified by preparative high performance liquid to yield 145 mg (100% purity, 64% yield) of title compound as a white solid. Log P=3.31. (M+H)=322.

Preparation Example 7: Preparation of N²-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]-N-methoxyvalinamide (Compound I.074) Step 1: Preparation of ethyl N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]valinate

To a solution of 154 mg (0.50 mmol) of 4,5-dibromo-3-methylthiophene-2-carboxylic acid and 183 mg (1.00 mmol) of DL-valine ethyl ester hydrochloride dissolved in 3 mL of tetrahydrofuran was added 0.21 mL (1.51 mmol) of triethylamine followed by 0.45 mL (0.75 mmol) of a 50% (w/w) propanephosphonic anhydride solution in ethyl acetate. The reaction mixture was stirred at room temperature for 2 hours. The reaction mixture was quenched with a saturated aqueous solution of sodium bicarbonate and extracted with ethyl acetate. Combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (gradient n-heptane/ethyl acetate) to yield 103 mg (95% purity, 45% yield) of title compound as a white solid. Log P=4.32. (M+H)=426.

Step 2: Preparation of N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]valine

To a solution of 164 mg (0.38 mmol) of ethyl N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]-valinate and in 3 mL of tetrahydrofuran was added dropwise 0.81 mL of a 1 M lithium hydroxide solution (0.81 mmol). The reaction was stirred at room temperature for 18 hours. The reaction mixture was diluted with ethyl acetate and a saturated aqueous sodium bicarbonate solution. The organic layer was washed twice with a saturated aqueous sodium bicarbonate solution. Combined aqueous layers were carefully acidified with a 37% (w/w) aqueous hydrochloric acid solution at 0° C. and extracted with ethyl acetate. Combined organic layers were dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to yield 151 mg (98% purity, 96% yield) of title compound as a white solid. Log P=2.92. (M+H)=398.

Step 3: Preparation of N²-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]-N-methoxyvalinamide (Compound I.074)

To a solution of 200 mg (0.50 mmol) of N-[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]valine, 52 mg (0.60 mmol) of O-methylhydroxylamine hydrochloride (1:1) and 300 mg (1.00 mmol) of 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one in 3 mL of dry tetrahydrofuran was added 140 μL (1.00 mmol) of triethylamine. The reaction mixture was stirred at room temperature for 17 hours. The resulting reaction mixture was concentrated under reduced pressure, diluted with water and extracted twice with dichloromethane. Combined organic layers were dried over anhydrous magnesium sulfate, filtrated and concentrated under reduced pressure. The residue was dissolved in dichloromethane, filtered through a silica gel cartridge and concentrated under reduced pressure. The residue was purified by preparative high performance liquid to yield 35 mg (100% purity, 16% yield) of title compound as a white solid. Log P=2.77. (M−H)=425.

Exemplary Compounds

The exemplary compounds according to the invention as shown in tables 1a and 1b were prepared in analogy with the examples provided above and/or in accordance with the general description of the processes herein disclosed.

The following table 1a and 1b illustrates in a non-limiting manner examples of compounds according to formula (I).

TABLE 1a Ex. No R¹ R² R³ W Y R⁴ R⁵ n R⁶ R⁷ 1.003 Br Br CH₃ O NH —CH₂—CH(CH═CH₂)— 0 — — 1.004 Br Br CH₃ O NH —CH₂—CH₂—O—CH₂— 0 — — 1.005 Br Br CH₃ O NH —CH₂—CH₂—CF₂—CH₂—CH₂— 0 — — 1.006 Br Br CH₃ O NH CH₂—OH H 0 — — 1.007 Br Br CH₃ O NH 2-methylpropyl H 0 — — 1.008 Br Br CH₃ O NH isopropyl H 0 — — 1.009 Br Br CH₃ O NH H H 0 — — 1.011 Br Br CH₃ O NH H H 0 — — 1.012 Br Br CH₃ O NH —CH₂—CH₂— 1 H H 1.013 Br Br CH₃ O NH H H 1 —CH₂—CH₂— 1.014 Br Br CH₃ O NH —CH₂—O—CH₂— 0 — — 1.015 Br Br CH₃ O NH —CH₂—S—CH₂— 0 — — 1.016 Br Br CH₃ O NH 2-amino-2-oxoethyl H 0 — — 1.017 Br Br CH₃ O NH —CH₂—CH₂— 1 —CH₂—CH₂— 1.018 Br Br CH₃ O NH 2,2,2-trifluoroethyl H 0 — — 1.019 Br Br CH₃ O NH H H 1 —CH₂—CH₂— 1.020 Br Br CH₃ O NH —CH₂—CH₂— 1 —CH₂—CH₂— 1.023 Br Br CH₃ S NH isopropyl H 0 — — 1.024 Br Br CH₃ O NH H H 0 — — 1.025 Br Br CH₃ O NH H H 0 — — 1.026 Br Br CH₃ O NH H H 0 — — 1.027 Br Br CH₃ O NH —CH₂—CH₂— 0 — — 1.028 Br Br CH₃ O NH isopropyl H 0 — — 1.029 Br Br CH₃ O NH phenyl H 0 — — 1.030 Br Br CH₃ O NH benzyl H 0 — — 1.031 Br Br CH₃ S NH isopropyl H 0 — — 1.032 Br Br CH₃ O NH cyclopropyl H 0 — — 1.033 Br Br CH₃ O NH 1H-imidazol-4-ylmethyl H 0 — — 1.034 Br Br CH₃ O NH methoxymethyl H 0 — — 1.035 Br Br CH₃ O NH 3-carbamimidamidopropyl H 0 — — 1.036 Br Br CH₃ O NH 1H-indol-3-ylmethyl H 0 — — 1.038 Cl Cl CH₃ O NH H H 1 H H 1.039 Cl Cl CH₃ O NH CH₂—OH H 0 — — 1.040 Cl Cl CH₃ O NH 1H-indol-3-ylmethyl H 0 — — 1.041 Cl Cl CH₃ O NH 2-methylpropyl H 0 — — 1.042 Cl Cl CH₃ O NH isopropyl H 0 — — 1.043 Cl Cl CH₃ O NH 2,2-difluoroethyl H 0 — — 1.044 Cl Cl CH₃ O NH methoxymethyl H 0 — — 1.045 Cl Cl CH₃ O NH 2-amino-2-oxoethyl H 0 — — 1.046 Cl Cl CH₃ O NH 3-amino-3-oxopropyl H 0 — — 1.047 Cl Cl CH₃ O NH —CH2—CH2—CH2— 0 — — 1.049 Cl Cl CH₃ O NH —CH2—CH2— 0 — — 1.050 Cl Cl CH₃ S NH —CH2—CH2— 0 — — 1.051 Br Br CH₃ O NH isopropyl H 0 — — 1.052 Br Br CH₃ O NH 2-amino-2-oxoethyl H 0 — — 1.053 Br Br CH₃ O NH 2-amino-2-oxoethyl H 0 — — 1.054 Cl Cl CH₃ O NH 2-amino-2-oxoethyl H 0 — — 1.055 Cl Cl CH₃ O NH 2-amino-2-oxoethyl H 0 — — 1.056 Br Br CH₃ O N—CH3 H H 0 — — 1.057 Cl Cl CH₃ O N—CH3 H H 0 — — 1.058 Br Br CH₃ O N—CH3 isopropyl H 0 — — 1.059 Cl Cl CH₃ O N—CH3 isopropyl H 0 — — 1.060 Cl Cl CH₃ S NH —CH₂—CH₂— 0 — — 1.061 Br Br CH₃ O NH isopropyl H 0 — — 1.062 Cl Cl CH₃ O NH H H 0 — — 1.063 Cl Cl CH₃ O NH —CH₂—CH₂— 0 — — 1.067 Cl Cl CH₃ O NH CH₂—OH H 0 — — 1.068 Cl Cl CH₃ O NH 2-amino-2-oxoethyl H 0 — — 1.069 Cl Cl CH₃ O NH 3-amino-3-oxopropyl H 0 — — 1.070 Cl Cl CH₃ O NH 1H-indol-3-ylmethyl H 0 — — 1.071 Br Br CH₃ O NH CH₂—OH H 0 — — 1.072 Br Br CH₃ O NH 3-amino-3-oxopropyl H 0 — — 1.073 Br Br CH₃ O NH 1H-indol-3-ylmethyl H 0 — — 1.074 Br Br CH₃ O NH isopropyl H 0 — — 1.075 Br Br CH₃ O NH isopropyl H 0 — — 1.076 Br Br CH₃ O NH 2-amino-2-oxoethyl H 0 — — 1.077 Br Br CH₃ O NH cyano H 0 — — 1.078 Cl Cl CH₃ O NH carboxymethyl H 0 — — 1.079 Cl Cl CH₃ O NH 3-carbamimidamidopropyl H 0 — — 1.080 Br Br CH₃ O NH cyclopropyl H 0 — — 1.081 Cl Cl CH₃ O NH cyclopropyl H 0 — — 1.082 Cl Cl CH₃ O NH —CH₂—CH₂— 1 H H 1.083 Cl Cl CH₃ O NH cyclopropyl H 0 — — 1.084 Cl Cl CH₃ O NH methoxycarbonyl H 0 — — 1.085 Cl Cl CH₃ O NH cyclopropylmethyl H 0 — — 1.086 Cl Cl CH₃ O NH cyclopropyl cyclopropyl 0 — — 1.087 Cl Cl CH₃ O NH ethoxycarbonyl H 0 — — 1.088 Cl Cl CH₃ O NH —CH₂—N(Boc)—CH₂— 0 — — 1.089 Br Br CH₃ O NH cyclopropyl H 0 — — 1.090 Br Br CH₃ O NH —CH₂—N(Boc)—CH₂— 0 — — 1.091 Br Br CH₃ O NH methoxycarbonyl H 0 — — 1.092 Br Br CH₃ O NH cyclopropylmethyl H 0 — — 1.093 Br Br CH₃ O NH cyclopropyl cyclopropyl 0 — — 1.094 Br Br CH₃ O NH ethoxycarbonyl H 0 — — 1.095 Cl Cl CH₃ O NH cyclopropyl H 0 — — 1.096 Cl Cl CH₃ O NH cyclopropyl H 0 — — 1.097 Br Br CH₃ O N—OCH₃ H H 0 — — 1.098 Cl Cl CH₃ O N—OCH₃ H H 0 — — 1.099 Cl Cl CH₃ S NH H H 0 — — 1.100 Br Br CH₃ S NH —CH₂—CH₂— 0 — — 1.101 Br Br CH₃ S NH —CH₂—CH₂— 0 — — 1.102 Br Br CH₃ S NH —CH₂—CH₂— 0 — — 1.103 Cl Cl CH₃ O NH 2-carboxyethyl H 0 — — 1.104 Br Br CH₃ O NH 2-carboxyethyl H 0 — — 1.106 Br Br CH₃ O NH —CH₂—CH₂—CH₂—CH₂— 0 — — 1.107 Br Br CH₃ O NH —CH₂—CH₂—O—CH₂—CH₂— 0 — — 1.108 Br Br CH₃ O NH 2,2-difluoroethyl H 0 — — 1.109 Br Br CH₃ O NH CH₃ H 1 H H 1.110 Cl Cl CH₃ O NH H H 0 — — 1.112 Br Br CH₃ O NH O—CH₂CH₃ isopropyl 0 — — 1.113 Cl Cl CH₃ S NH H H 0 — — 1.114 Cl Cl CH₃ O N—OH cyclopropyl H 0 — — 1.115 Br Br CH₃ O NH isopropyl H 0 — — 1.116 Cl Cl CH₃ O N—OH H H 0 — — 1.117 Cl Cl CH₃ O NH 2-(acetylthio)ethyl H 0 — — 1.118 Cl Cl CH₃ O NH 2-methoxy-2-oxoethyl H 0 — — 1.119 Cl Cl CH₃ O NH [(dimethylaminocarbonyl)thio]methyl H 0 — — 1.120 Cl Cl CH₃ O NH (ethylcarbamoylthio)methyl H 0 — — 1.121 Cl Cl CH₃ O NH (methylcarbamothioylthio)methyl H 0 — — 1.122 Cl Cl CH₃ O NH 3-methoxy-3-oxopropyl H 0 — — 1.123 Cl Cl CH₃ O NH 2-ethoxy-2-oxoethyl H 0 — — 1.124 Cl Cl CH₃ O NH 3-ethoxy-3-oxopropyl H 0 — — 1.125 Cl Cl CH₃ O NH 2-tert-butoxy-2-oxoethyl H 0 — — 1.126 Cl Cl CH₃ O NH (acetylthio)methyl H 0 — — 1.127 Br Br CH₃ S NH —CH₂—CH₂— 0 — — 1.128 Br Br CH₃ O NH —CH₂—CH₂— 0 — — 1.129 Br Br CH₃ O NH —CH₂—CH₂— 0 — — 1.130 Br Br CH₃ O NH —CH₂—CH₂— 0 — — 1.131 Br Br CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.132 Br Br CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.133 Br Br CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.134 Br Br CH₃ O NH —CH₂—CH₂— 0 — — 1.135 Br Br CH₃ O NH —CH₂—CH₂— 0 — — 1.136 Br Br CH₃ O NH 3-methoxy-3-oxopropyl H 0 — — 1.137 Br Br CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.138 Br Br CH₃ O NH 3-amino-3-oxopropyl H 0 — — 1.139 Br Br CH₃ O NH —CH₂—CH₂—O—CH₂—CH₂— 0 — — 1.140 Cl Cl CH₃ O NH cyclopropyl H 0 — — 1.141 Cl Cl CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.142 Cl Cl CH₃ O NH —CH₂—C(CH₃)₂—CH₂— 0 — — 1.143 Cl Cl CH₃ O NH —CH₂—CF₂—CH₂— 0 — — 1.144 Cl Cl CH₃ O NH —CH₂—O—CH₂— 0 — — 1.145 Cl Cl CH₃ O NH —CH₂—CF₂—CH₂— 0 — — 1.146 Cl Cl CH₃ O NH —CH₂—S—CH₂— 0 — — 1.148 Cl Cl CH₃ O NH CH₂—OH H 0 — — 1.149 Br Br CH₃ S NH CH₃ H 0 — — 1.150 Br Br CH₃ S NH CH₃ H 0 — — 1.152 Br Br CH₃ O NH cyclopropyl CH₃ 0 — — 1.153 Cl Cl CH₃ O NH cyclopropyl H 0 — — 1.154 Cl Cl CH₃ O NH cyclopropyl H 0 — — 1.155 Cl Cl CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.156 Cl Cl CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.157 Cl Cl CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.158 Cl Cl CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.159 Cl Cl CH₃ O NH —CH₂—CH₂— 0 — — 1.160 Cl Cl CH₃ O NH —CH₂—CH₂— 0 — — 1.161 Cl Cl CH₃ O NH cyclopropyl H 0 — — 1.164 Cl Cl CH₃ O NH CF₃ H 0 — — 1.165 Cl Cl CH₃ O NH thiophen-2-yl H 0 — — 1.166 Cl Cl CH₃ O NH benzyl CH₃ 0 — — 1.168 Cl Cl CH₃ O N—cPr H H 0 — — 1.169 Br Br CH₃ O NH —CH₂—CH₂—S—CH₂—CH₂— 0 — — 1.171 Cl Cl CH₃ O NH —CH₂—CH₂—CH₂— 0 — — 1.172 Cl Cl CH₃ S NH H H 0 — — 1.173 Br Br CH₃ S NH CH₃ H 0 — — 1.174 Cl Cl CH₃ O NH CH₃ CH₃ 0 — — 1.175 Cl Cl CH₃ O NH —CH₂—CH₂—CH₂ 0 — — 1.176 Cl Cl CH₃ O NH CH₃ CH₃ 0 — — 1.177 Br Br CH₃ O NH —CH₂—S—CH₂—CH₂—CH₂— 0 — — Ex. No Z LogP Enantiomer Optical Rotation 1.003 methoxycarbonyl 3.48^([a]) 1.004 methoxycarbonyl 2.84^([a]) 1.005 methoxycarbonyl 3.83^([a]) 1.006 ethoxycarbonyl 2.58^([a]) 1.007 ethylsulfanylcarbonyl 5.03^([a]) 1.008 ethylsulfanylcarbonyl 4.74^([a]) 1.009 benzylsulfanylcarbonyl 4 34^([a]) 1.011 phenylsulfanylcarbonyl 4.10^([a]) 1.012 methoxycarbonyl 3.07^([a]) 1.013 ethoxycarbonyl 3.79^([a]) 1.014 ethoxycarbonyl 2.90^([a]) 1.015 methoxycarbonyl 3.31^([a]) 1.016 ethoxycarbonyl 2.26^([a]) 1.017 ethoxycarbonyl 4.37^([a]) 1.018 ethoxycarbonyl 3.99^([a]) 1.019 carboxy 2.50^([a]) 1.020 isopropyloxycarbonyl 4.87^([a]) 1.023 ethoxycarbonyl 5.22^([a]) 1.024 [[1-(ethoxycarbonyl)cyclopropyl]amino]carbonyl 2.55^([a]) 1.025 [(1-carboxycyclopropyl)amino]carbonyl 1.95^([a]) 1.026 cyano 2.59^([a]) 1.027 cyano 2.80^([a]) 1.028 cyano 3.64^([a]) 1.029 cyano 3.85^([a]) 1.030 cyano 4.01^([a]) 1.031 carboxy 3.72^([a]) 1.032 methoxycarbonyl 3.41^([a]) 1.033 methoxycarbonyl 1.50^([a]) 1.034 ethoxycarbonyl 3.46^([a]) 1.035 methoxycarbonyl 1.74^([a]) (S) 1.036 ethoxycarbonyl 4.15^([a]) 1.038 ethoxycarbonyl 3.06^([a]) 1.039 ethoxycarbonyl 2.48^([a]) 1.040 ethoxycarbonyl 4.08^([a]) 1.041 ethylsulfanylcarbonyl 5.00^([a]) 1.042 ethylsulfanylcarbonyl 4.69^([a]) 1.043 methoxycarbonyl 3.25^([a]) 1.044 ethoxycarbonyl 3.37^([a]) 1.045 ethoxycarbonyl 2.28^([a]) 1.046 methoxycarbonyl 2.06^([a]) (S) −24.9° (c = 0.89, DMSO, 25° C.) 1.047 ethoxycarbonyl 3.67^([a]) 1.049 ethylsulfanylcarbonyl 3.67^([a]) 1.050 methoxycarbonyl 3.68^([a]) 1.051 aminocarbonyl 2.58^([a]) 1.052 methoxycarbonyl 2.12^([a]) (R) 1.053 methoxycarbonyl 2.12^([a]) (S) −8.9° (c = 0.9, DMSO, 25° C.) 1.054 methoxycarbonyl 2.05^([a]) (R) 1.055 methoxycarbonyl 2.02^([a]) (S) −2.1° (c = 2.93, DMSO, 25° C.) 1.056 ethoxycarbonyl 3.23^([a]) 1.057 ethoxycarbonyl 3.15^([a]) 1.058 ethoxycarbonyl 4.51^([a]) 1.059 ethoxycarbonyl 4.44^([a]) 1.060 carboxy 2.84^([a]) 1.061 [methoxy(methyl)amino]carbonyl 3.71^([a]) 1.062 aminocarbonyl 1.75^([a]) 1.063 aminocarbonyl 1.96^([a]) 1.067 carboxy 1.84^([a]) 1.068 carboxy 1.73^([a]) 1.069 carboxy 1.70^([a]) 1.070 carboxy 3.12^([a]) 1.071 carboxy 1.92^([a]) 1.072 carboxy 1.77^([a]) 1.073 carboxy 3.07^([a]) 1.074 (methoxyamino)carbonyl 2.77^([a]) 1.075 (cyanomethylamino)carbonyl 2.92^([a]) 1.076 carboxy 1.73^([a]) 1.077 ethoxycarbonyl 3.22^([a]) 1.078 methoxycarbonyl 2.28^([a]) (S) 1.079 methoxycarbonyl 1.68^([a]) (S) −1.9° (c = 1.05, DMSO, 25° C) 1.080 carboxy 2.67^([a]) 1.081 methoxycarbonyl 3.31^([a]) 1.082 methoxycarbonyl 2.98^([a]) 1.083 ethoxycarbonyl 3.76^([a]) 1.084 methoxycarbonyl 3.01^([a]) 1.085 ethoxycarbonyl 4.23^([a]) 1.086 methoxycarbonyl 3.94^([a]) 1.087 ethoxycarbonyl 3.81^([a]) 1.088 ethoxycarbonyl 4.15^([a]) 1.089 ethoxycarbonyl 3.84^([a]) 1.090 ethoxycarbonyl 4.23^([a]) 1.091 methoxycarbonyl 3.10^([a]) 1.092 ethoxycarbonyl 4.30^([a]) 1.093 methoxycarbonyl 4.01^([a]) 1.094 ethoxycarbonyl 3.87^([a]) 1.095 carboxy 2.59^([a]) 1.096 [[carboxy(cyclopropyl)methyl]amino]carbonyl 2.67^([a]) 1.097 ethoxycarbonyl 3.93^([a]) 1.098 ethoxycarbonyl 3.87^([a]) 1.099 ethoxycarbonyl 3.92^([a]) 1.100 ethoxycarbonyl 4.15^([a]) 1.101 methoxycarbonyl 3.78^([a]) 1.102 carboxy 2.91^([a]) 1.103 methoxycarbonyl 2.39^([a]) (S) +9.9° (c = 1.01, CDCl3, 25° C.) 1.104 methoxycarbonyl 2.46^([a]) (S) +3.8° (c = 1.04, CDCl3, 25° C.) 1.106 ethoxycarbonyl 4.09^([a]) 1.107 methoxycarbonyl 2.82^([a]) 1.108 methoxycarbonyl 3.33^([a]) 1.109 methoxycarbonyl 3.14^([a]) 1.110 methylcarbamoyl 1.92^([a]) 1.112 ethoxycarbonyl 4.80^([a]) 1.113 methoxycarbonyl 3.60^([a]) 1.114 methoxycarbonyl 3.13^([a]) 1.115 (hydroxyamino)carbonyl 2.31^([a]) 1.116 ethoxycarbonyl 2.95^([a]) 1.117 methoxycarbonyl 3.59^([a]) 1.118 methoxycarbonyl 3.00^([a]) (S) +57.9° (c = 0.9, CHCl3, 25° C.) 1.119 methoxycarbonyl 3.35^([a]) (R) −15.9° (c = 1.13, CHCl3, 25° C.) 1.120 methoxycarbonyl 3.22^([a]) (R) −3.7° (c = 1.08, CHCl3, 25° C.) 1.121 methoxycarbonyl 3.33^([a]) (R) 1.122 methoxycarbonyl 3.08^([a]) (S) +16.9° (c = 0.83, CHCl3, 25° C.) 1.123 ethoxycarbonyl 3.76^([a]) (S) +50.8° (c = 1.18, CHCl3, 25° C.) 1.124 ethoxycarbonyl 3.84^([a]) (S) +16.8° (c = 1.19, CHCl3, 25° C.) 1.125 methoxycarbonyl 4.17^([a]) (S) +50.3° (c = 0.99, CHCl3, 25° C.) 1.126 ethoxycarbonyl 3.51^([a]) 1.127 cyclobutyloxycarbonyl 4.66^([a]) 1.128 ethylsulfanylcarbonyl 3.81^([a]) 1.129 aminocarbonyl 2.07^([a]) 1.130 methylcarbamoyl 2.21^([a]) 1.131 methoxycarbonyl 3.40^([a]) 1.132 ethoxycarbonyl 3.81^([a]) 1.133 propoxycarbonyl 4.23^([a]) 1.134 (propylthio)carbonyl 4.26^([a]) 1.135 (cyclobutylamino)carbonyl 2.94^([a]) 1.136 methoxycarbonyl 3.17^([a]) (S) −17.5° (c = 1.26, MeOH, 25° C.) 1.137 carboxy 2.63^([a]) 1.138 methoxycarbonyl 2.13^([a]) (S) −6.5° (c = 0.93, DMSO, 25° C.) 1.139 ethoxycarbonyl 3.17^([a]) 1.140 phenylmethoxycarbonyl 4.53^([a]) 1.141 isopropyloxycarbonyl 4.05^([a]) 1.142 methoxycarbonyl 4.05^([a]) 1.143 methoxycarbonyl 3.43^([a]) 1.144 methoxycarbonyl 2.52^([a]) 1.145 tert-butoxycarbonyl 4.48^([a]) 1.146 ethoxycarbonyl 3.60^([a]) 1.148 ethoxycarbonyl 2.53^([a]) (S) +18.8° (c = 0.96, MeOH, 25° C.) 1.149 methoxycarbonyl 4.05^([a]) 1.150 ethoxycarbonyl 4.38^([a]) 1.152 cyano 3.50^([a]) 1.153 cyclobutyloxycarbonyl 4.44^([a]) 1.154 isopropyloxycarbonyl 4.23^([a]) 1.155 cyclopropylmethoxycarbonyl 4.19^([a]) 1.156 tert-butoxycarbonyl 4.55^([a]) 1.157 butoxycarbonyl 4.59^([a]) 1.158 cyclohexyloxycarbonyl 5.08^([a]) 1.159 carbamothioyl 2.54^([a]) 1.160 methylcarbamoyl 2.12^([a]) 1.161 tert-butoxycarbonyl 4.70^([a]) 1.164 ethoxycarbonyl 4.07^([a]) 1.165 methoxycarbonyl 3.81^([a]) 1.166 methoxycarbonyl 4.60^([a]) 1.168 ethoxycarbonyl 3.75^([a]) 1.169 cyano 3.59^([a]) 1.171 methoxycarbonyl 3.50^([a]) 1.172 carboxy 2.71^([a]) 1.173 carboxy 3.05^([a]) 1.174 carboxy 2.43^([a]) 1.175 carboxy 2.62^([a]) 1.176 methoxycarbony 3.16^([a]) 1.177 cyano 3.50^([a]) Notes: Optical rotation: concentration c is expressed in g/100 mL; Boc means tert-butyloxycarbonyl; cPr means cyclopropyl

TABLE 2a Ex. N^(o) R¹ R² R³ W Y

LogP Optical Rotation I.001 Br Br CH₃ O NH 2,2-dimethyl-4-oxothietan-3-yl 3.99^([a]) I.002 Br Br CH₃ O NH 2-oxothiolan-3-yl 3.04^([a]) I.010 Br Br CH₃ O NH (3S)-2-oxothiolan-3-yl 3.04^([a]) −18.6° (c = 1.08, DMSO, 25° C.) I.021 Br Br CH₃ O NH 2-oxooxolan-3-yl 2.41^([a]) I.022 Br Br CH₃ O NH 2-oxopiperidin-3-yl 2.10^([a]) I.037 Cl Cl CH₃ O NH 2-oxothiolan-3-yl 2.86^([a]) I.048 Cl Cl CH₃ O NH (2S)-3-carboxy-1-oxo-1-[[(2S)-1- 3.09^([a]) −9.5° (c = 1.05, DMSO, 25° C.) methoxy-1-oxo-3-phenylpropan-2-yl]amino]propan-2-yl I.064 Br Br CH₃ O NH 2-oxopyrrolidin-3-yl 1.93^([a]) I.065 Br Br CH₃ O NH 5-oxopyrrolidin-3-yl 1.89^([a]) I.066 Br Br CH₃ O NH 2-oxopiperidin-4-yl 1.93^([a]) I.105 Br Br CH₃ O NH (2S)-3-carboxyl-1-oxo-1-[[(2S)-1- 3.11^([a]) methoxy-1-oxo-3-phenylpropan-2-yl]amino]propan-2-yl I.111 Cl Cl CH₃ O NH (3S)-2-oxothiolan-3-yl 2.97^([b]) −21.3° (c = 0.85, DMSO, 25° C.) I.147 Cl Cl CH₃ O NH 2-oxooxolan-3-yl 2.40^([a]) I.151 Br Br CH₃ O NH 1-cyano-4-cyclohexylcyclohexyl 6.06^([a]) I.162 Cl Cl CH₃ O NH (3S)-2-oxopiperidin-3-yl 2.12^([a]) +78.1° (c = 1.05, CDCl3, 25° C.) I.163 Cl Cl CH₃ O NH 2-oxoazepan-3-yl 2.67^([a]) I.167 Cl Cl CH₃ O NH (3S)-2-oxooxolan-3-yl 2.34^([a]) −16.6° (c = 0.48, MeOH, 25° C.) I.170 Br Br CH₃ O NH 1-cyano-4-phenylcyclohexyl 4.78^([a]) Notes: “*” is linked to Y; Optical rotation: concentration c is expressed in g/100 mL. In the above tables, measurement of LogP values was performed according to EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on reversed phase columns with the following methods: ^([a])LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% formic acid in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). ^([b])LogP value is determined by measurement of LC-UV, in a neutral range, with 0.001 molar ammonoium acetate solution in water and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile). ^([c])LogP value is determined by measurement of LC-UV, in an acidic range, with 0.1% phosphoric acid and acetonitrile as eluent (linear gradient from 10% acetonitrile to 95% acetonitrile).

If more than one Log P value is available within the same method, all the values are given and separated by “+”.

Calibration was done with straight-chain alkan2-ones (with 3 to 16 carbon atoms) with known Log P values (measurement of Log P values using retention times with linear interpolation between successive alkanones). Lambda-max-values were determined using UV-spectra from 200 nm to 400 nm and the peak values of the chromatographic signals.

NMR-Peak Lists

Table A provides the NMR data (¹H) of some compounds disclosed in the above tables.

¹H-NMR data of selected examples are written in form of ¹H-NMR-peak lists. To each signal peak are listed the δ-value in ppm and the signal intensity in round brackets. Between the δ-value—signal intensity pairs are semicolons as delimiters.

The peak list of an example has therefore the form:

δ₁ (intensity₁); δ₂ (intensity₂); . . . ; δ_(i) (intensity_(i)); . . . ; δ_(n) (intensity_(n))

Intensity of sharp signals correlates with the height of the signals in a printed example of a NMR spectrum in cm and shows the real relations of signal intensities. From broad signals several peaks or the middle of the signal and their relative intensity in comparison to the most intensive signal in the spectrum can be shown.

For calibrating chemical shift for ¹H spectra, we use tetramethylsilane and/or the chemical shift of the solvent used, especially in the case of spectra measured in DMSO. Therefore, in NMR peak lists, tetramethylsilane peak can occur but not necessarily.

The ¹H-NMR peak lists are similar to classical ¹H-NMR prints and contains therefore usually all peaks, which are listed at classical NMR-interpretation.

Additionally they can show like classical ¹H-NMR prints signals of solvents, stereoisomers of the target compounds, which are also object of the invention, and/or peaks of impurities.

To show compound signals in the delta-range of solvents and/or water the usual peaks of solvents, for example peaks of DMSO in DMSO-D₆ and the peak of water are shown in our ¹H-NMR peak lists and have usually on average a high intensity.

The peaks of stereoisomers of the target compounds and/or peaks of impurities have usually on average a lower intensity than the peaks of target compounds (for example with a purity >90%).

Such stereoisomers and/or impurities can be typical for the specific preparation process. Therefore, their peaks can help to recognize the reproduction of our preparation process via “side-products-fingerprints”.

An expert, who calculates the peaks of the target compounds with known methods (MestreC, ACD-simulation, but also with empirically evaluated expectation values) can isolate the peaks of the target compounds as needed optionally using additional intensity filters. This isolation would be similar to relevant peak picking at classical ¹H-NMR interpretation.

Further details of NMR-data description with peak lists you find in the publication “Citation of NMR Peaklist Data within Patent Applications” of the Research Disclosure Database Number 564025.

TABLE A NMR peak lists I.001: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2983 (0.8); 6.8212 (0.7); 6.7960 (0.7); 5.8215 (2.6); 5.7958 (2.5); 2.5654 (0.4); 2.5479 (16.0); 1.9393 (11.7); 1.7273 (11.2); 1.6815 (0.5); 0.0320 (0.9) I.002: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2984 (4.8); 6.2939 (0.5); 6.2812 (0.5); 4.6626 (0.5); 4.6451 (0.5); 4.6401 (0.6); 4.6213 (0.7); 4.6023 (0.6); 4.5972 (0.6); 4.5799 (0.5); 3.5044 (0.4); 3.4876 (0.4); 3.4661 (0.9); 3.4493 (1.0); 3.4259 (0.9); 3.4092 (0.9); 3.3835 (0.8); 3.3635 (0.8); 3.3599 (0.8); 3.3490 (0.4); 3.3455 (0.4); 3.3254 (0.4); 3.3218 (0.3); 3.1621 (0.3); 3.1580 (0.4); 3.1453 (0.4); 3.1404 (0.5); 3.1353 (0.4); 3.1210 (0.6); 3.1179 (0.6); 3.1038 (0.4); 3.0990 (0.6); 3.0941 (0.4); 3.0813 (0.3); 2.5847 (16.0); 2.1013 (0.3); 2.0837 (0.7); 2.0602 (0.7); 2.0419 (0.7); 2.0181 (0.6); 1.5925 (1.9); 0.0368 (6.3) I.003: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.0417 (2.7); 7.9528 (0.4); 5.7125 (0.5); 5.6872 (0.7); 5.6696 (0.7); 5.6645 (0.7); 5.6467 (0.8); 5.6443 (0.9); 5.6215 (0.7); 5.3427 (1.3); 5.3386 (1.4); 5.2999 (1.0); 5.2957 (1.1); 5.1444 (1.4); 5.1400 (1.3); 5.1187 (1.2); 5.1141 (1.3); 3.6224 (16.0); 3.3335 (20.0); 2.8937 (2.8); 2.7347 (2.5); 2.5263 (0.5); 2.5129 (8.0); 2.5087 (15.8); 2.5043 (20.6); 2.4999 (15.7); 2.4302 (0.5); 2.4176 (15.1); 2.3321 (0.5); 2.3101 (1.2); 2.2888 (1.2); 2.2665 (0.5); 1.7301 (1.1); 1.7168 (1.2); 1.7102 (1.2); 1.6969 (1.1); 1.4633 (1.1); 1.4502 (1.2); 1.4398 (1.2); 1.4267 (1.0); 1.2400 (0.5); −0.0002 (0.6) I.004: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2995 (1.2); 6.0510 (2.1); 3.9463 (1.0); 3.9325 (1.8); 3.9176 (1.2); 3.9065 (1.5); 3.8923 (2.7); 3.8782 (1.4); 3.7971 (16.0); 3.7537 (1.5); 3.7456 (1.7); 3.7132 (2.5); 3.6809 (1.2); 3.6729 (1.1); 2.5539 (15.6); 2.3644 (1.0); 2.3503 (1.1); 2.3314 (1.2); 2.3176 (2.2); 2.3036 (1.5); 2.2848 (1.5); 2.2709 (1.3); 2.0679 (2.2); 2.0214 (1.6); 1.4530 (0.6); 1.4024 (0.5); 1.3615 (0.9); 1.3157 (1.7); 1.2861 (4.4); 0.9100 (0.7); 0.8837 (1.2); 0.8614 (1.2); 0.0309 (1.2) I.005: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7098 (2.3); 3.6425 (16.0); 3.3627 (30.3); 2.5279 (0.4); 2.5146 (7.0); 2.5102 (14.2); 2.5058 (18.9); 2.5013 (14.5); 2.4970 (7.5); 2.4032 (15.0); 2.3565 (0.6); 2.2386 (1.0); 2.2297 (1.1); 2.0438 (1.1); 2.0108 (2.0); 1.9950 (1.4); 1.9796 (1.6); 1.9546 (1.7); 1.9342 (0.5); −0.0002 (0.4) I.006: ¹H-NMR(600.4 MHz, d₆-DMSO): δ = 8.3548 (1.0); 8.3423 (1.0); 5.0559 (0.6); 5.0461 (1.4); 5.0361 (0.7); 4.4668 (0.5); 4.4583 (1.0); 4.4543 (0.6); 4.4495 (0.6); 4.4458 (1.0); 4.4370 (0.5); 4.1425 (0.6); 4.1399 (0.7); 4.1306 (2.2); 4.1281 (2.2); 4.1187 (2.2); 4.1163 (2.1); 4.1069 (0.7); 4.1045 (0.7); 3.7807 (1.3); 3.7710 (2.8); 3.7616 (1.9); 3.3256 (11.9); 3.3233 (12.5); 3.3201 (19.7); 2.5092 (3.9); 2.5062 (8.6); 2.5031 (12.2); 2.5000 (8.6); 2.4970 (3.9); 2.4395 (16.0); 1.2122 (4.6); 1.2004 (9.6); 1.1886 (4.4) I.007: ¹H-NMR(600.4 MHz, d₆-DMSO): δ = 8.8300 (1.0); 8.8171 (1.0); 7.9525 (1.2); 4.5409 (0.4); 4.5341 (0.5); 4.5280 (0.5); 4.5216 (0.8); 4.5159 (0.5); 4.5101 (0.5); 4.5030 (0.5); 3.3661 (2.0); 3.3401 (9.0); 3.3368 (11.5); 3.3307 (26.0); 3.3287 (34.5); 2.8940 (11.6); 2.8322 (1.3); 2.8199 (4.0); 2.8076 (4.1); 2.7953 (1.3); 2.7350 (9.0); 2.5105 (5.6); 2.5074 (12.5); 2.5044 (17.6); 2.5013 (12.6); 2.4982 (5.7); 2.4408 (16.0); 1.7433 (0.4); 1.7360 (0.5); 1.7251 (0.4); 1.7212 (0.6); 1.7177 (0.6); 1.7139 (0.7); 1.7031 (0.4); 1.6958 (0.6); 1.6669 (0.4); 1.6626 (0.4); 1.6556 (0.4); 1.6518 (0.4); 1.6443 (0.4); 1.6410 (0.4); 1.5962 (0.7); 1.5890 (0.7); 1.5806 (0.4); 1.5739 (1.0); 1.5671 (0.5); 1.5585 (0.4); 1.5518 (0.4); 1.1702 (4.5); 1.1579 (9.4); 1.1456 (4.4); 0.9156 (6.5); 0.9047 (6.3); 0.8757 (6.1); 0.8650 (6.1) I.008: ¹H-NMR(600.4 MHz, d₆-DMSO): δ = 8.7446 (1.2); 8.7314 (1.2); 4.3480 (1.0); 4.3353 (1.6); 4.3232 (1.0); 3.3789 (2.0); 3.3517 (9.9); 3.3489 (11.0); 3.3450 (15.9); 3.3399 (38.0); 3.3377 (48.9); 2.8537 (1.2); 2.8414 (4.0); 2.8292 (4.1); 2.8169 (1.4); 2.5106 (5.6); 2.5075 (12.5); 2.5045 (17.6); 2.5014 (12.6); 2.4983 (5.7); 2.4215 (16.0); 2.4061 (0.6); 2.2294 (0.6); 2.2180 (1.1); 2.2066 (1.1); 2.1953 (0.6); 1.1771 (4.5); 1.1648 (9.5); 1.1525 (4.4); 1.0953 (0.5); 1.0839 (0.5); 0.9504 (7.3); 0.9470 (7.2); 0.9391 (7.4); 0.9357 (7.0) I.009: ¹H-NMR(499.9 MHz, d₆-DMSO): δ = 8.9097 (0.9); 8.8981 (1.7); 8.8864 (0.8); 7.3194 (0.6); 7.3159 (0.5); 7.3037 (4.7); 7.2990 (5.0); 7.2927 (16.0); 7.2821 (1.0); 7.2556 (0.9); 7.2501 (1.1); 7.2445 (0.9); 7.2417 (0.9); 7.2384 (1.1); 7.2345 (0.7); 7.2310 (0.5); 7.2271 (0.5); 4.1775 (5.2); 4.1657 (5.2); 4.1329 (11.7); 3.3188 (2.9); 2.5049 (1.7); 2.5014 (2.2); 2.4979 (1.6); 2.4585 (20.6) I.010: ¹H-NMR(499.9 MHz, d₆-DMSO): δ = 8.5561 (15.5); 8.5396 (16.0); 5.7521 (1.3); 4.7993 (5.7); 4.7840 (9.4); 4.7737 (8.1); 4.7689 (8.0); 4.7582 (10.0); 4.7432 (6.3); 3.4706 (5.2); 3.4599 (6.3); 3.4476 (11.5); 3.4370 (11.8); 3.4245 (9.5); 3.4138 (8.3); 3.3408 (14.8); 3.3228 (694.8); 3.3075 (24.6); 2.5529 (1.0); 2.5043 (39.4); 2.5010 (49.0); 2.4976 (41.3); 2.4804 (13.0); 2.4687 (11.2); 2.4568 (7.3); 2.4248 (170.1); 2.3693 (0.7); 2.3621 (0.7); 2.3021 (3.4); 2.2881 (4.2); 2.2775 (9.2); 2.2633 (9.7); 2.2528 (9.2); 2.2385 (8.7); 2.2282 (3.7); 2.2141 (2.9); 1.2323 (0.4) I.011: ¹H-NMR(500.1 MHz, CDCl3): δ = 7.4442 (16.0); 7.4170 (0.3); 7.2594 (5.7); 6.3949 (0.8); 4.4807 (4.5); 4.4699 (4.5); 4.3483 (0.4); 2.9553 (0.5); 2.8825 (0.5); 2.5604 (13.6); 1.5662 (0.9); −0.0002 (6.6) I.012: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.5177 (2.0); 3.5913 (16.0); 3.3261 (6.2); 2.6223 (6.6); 2.5254 (0.3); 2.5119 (6.3); 2.5076 (12.6); 2.5031 (16.7); 2.4986 (12.5); 2.4942 (6.4); 2.3515 (15.5); 0.8364 (0.4); 0.8109 (3.3); 0.7962 (2.4); 0.7919 (3.4); 0.7662 (0.4); −0.0002 (4.3) I.013: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.2464 (0.4); 8.2326 (0.9); 8.2189 (0.4); 4.0940 (1.4); 4.0763 (4.5); 4.0586 (4.6); 4.0408 (1.5); 3.4931 (3.4); 3.4790 (3.4); 3.3364 (33.4); 2.5210 (0.3); 2.5125 (5.0); 2.5080 (10.3); 2.5035 (13.8); 2.4989 (10.0); 2.4943 (4.8); 2.3789 (16.0); 1.1922 (4.8); 1.1745 (9.8); 1.1567 (4.6); 1.0969 (0.9); 1.0857 (2.4); 1.0784 (3.3); 1.0695 (1.4); 0.9730 (1.4); 0.9639 (3.3); 0.9566 (2.5); 0.9452 (1.0) I.014: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.4283 (2.1); 4.8802 (3.8); 4.8632 (4.3); 4.6639 (4.3); 4.6469 (3.7); 4.2153 (1.4); 4.1975 (4.4); 4.1798 (4.4); 4.1621 (1.4); 3.3361 (10.8); 2.5128 (4.4); 2.5084 (9.0); 2.5038 (12.6); 2.4992 (8.6); 2.4947 (4.2); 2.4436 (16.0); 1.2187 (4.7); 1.2010 (9.7); 1.1833 (4.5) I.015: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.4178 (1.8); 3.6915 (16.0); 3.6874 (4.4); 3.6610 (4.2); 3.4357 (4.0); 3.4095 (3.3); 3.3342 (21.3); 2.8921 (0.4); 2.7334 (0.4); 2.7323 (0.4); 2.5126 (4.4); 2.5081 (9.1); 2.5035 (11.9); 2.4989 (8.6); 2.4944 (4.1); 2.4300 (14.7) I.016: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6220 (1.2); 8.6028 (1.2); 7.4538 (1.0); 7.0061 (1.0); 4.7116 (0.5); 4.6977 (0.6); 4.6930 (1.1); 4.6790 (1.0); 4.6742 (0.7); 4.6603 (0.5); 4.1298 (1.3); 4.1122 (4.1); 4.0944 (4.2); 4.0767 (1.3); 3.3334 (26.8); 2.8918 (0.4); 2.7321 (0.4); 2.7058 (0.6); 2.6920 (0.6); 2.6668 (1.6); 2.6531 (1.4); 2.6318 (1.5); 2.6133 (1.5); 2.5928 (0.6); 2.5744 (0.7); 2.5212 (0.4); 2.5124 (5.2); 2.5079 (10.8); 2.5033 (14.6); 2.4987 (10.6); 2.4942 (5.1); 2.4147 (16.0); 1.1956 (4.7); 1.1779 (9.9); 1.1601 (4.5) I.017: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.2306 (1.8); 4.1248 (1.4); 4.1071 (4.4); 4.0893 (4.4); 4.0716 (1.4); 3.3377 (38.8); 2.5264 (0.3); 2.5217 (0.3); 2.5130 (5.2); 2.5085 (10.6); 2.5039 (14.2); 2.4993 (10.2); 2.4947 (4.9); 2.3663 (16.0); 1.2323 (4.8); 1.2146 (9.8); 1.1968 (4.6); 1.0584 (0.4); 1.0427 (1.7); 1.0354 (4.0); 1.0301 (2.0); 1.0163 (2.1); 1.0114 (4.0); 1.0040 (1.7); 0.9885 (0.4); 0.9009 (0.9); 0.8868 (2.3); 0.8822 (2.4); 0.8693 (1.1); 0.7262 (1.2); 0.7131 (2.3); 0.7086 (2.4); 0.6943 (0.8) I.018: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.9309 (1.1); 8.9111 (1.1); 4.7018 (0.4); 4.6920 (0.4); 4.6775 (0.6); 4.6723 (0.5); 4.6679 (0.5); 4.6577 (0.4); 4.6477 (0.4); 4.1800 (0.6); 4.1744 (0.7); 4.1717 (0.4); 4.1622 (2.0); 4.1567 (2.1); 4.1444 (2.1); 4.1390 (2.0); 4.1296 (0.3); 4.1266 (0.7); 4.1213 (0.6); 3.3413 (35.9); 2.9231 (0.8); 2.9132 (0.4); 2.8950 (1.1); 2.8851 (0.5); 2.8681 (0.8); 2.8567 (0.4); 2.8428 (0.5); 2.5134 (5.0); 2.5089 (10.3); 2.5043 (13.7); 2.4997 (10.0); 2.4952 (4.8); 2.4201 (16.0); 1.2161 (4.6); 1.1983 (9.7); 1.1806 (4.4) I.019: ¹H-NMR(499.9 MHz, d₆-DMSO): δ = 8.1984 (0.6); 8.1876 (1.1); 8.1766 (0.6); 3.4748 (3.4); 3.4635 (3.3); 3.3242 (5.7); 2.5163 (1.6); 2.5128 (3.2); 2.5092 (4.4); 2.5056 (3.3); 2.5022 (1.7); 2.3909 (16.0); 1.0746 (1.1); 1.0663 (2.8); 1.0604 (3.3); 1.0533 (1.3); 0.9257 (1.4); 0.9183 (3.2); 0.9124 (3.0); 0.9040 (1.1) I.020: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2988 (2.0); 6.9949 (1.0); 5.0971 (0.4); 5.0763 (1.0); 5.0554 (1.4); 5.0346 (1.0); 5.0138 (0.4); 2.5454 (16.0); 1.6654 (1.9); 1.2763 (15.6); 1.2554 (15.4); 1.2248 (0.8); 1.2147 (1.0); 1.2079 (2.1); 1.1984 (3.2); 1.1870 (1.4); 1.1569 (0.4); 1.1377 (0.4); 1.1080 (1.5); 1.0963 (3.1); 1.0868 (2.1); 1.0801 (1.0); 1.0703 (1.7); 1.0507 (2.5); 1.0462 (2.8); 1.0275 (1.3); 0.7993 (1.2); 0.7802 (2.6); 0.7760 (2.6); 0.7559 (0.9); 0.0329 (2.5) I.021: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7206 (0.6); 8.7050 (0.6); 8.3140 (0.9); 4.7440 (0.4); 4.7283 (0.4); 4.4227 (0.4); 4.4185 (0.5); 4.4007 (1.2); 4.3964 (1.1); 4.3786 (0.7); 4.3742 (0.6); 4.2960 (0.5); 4.2796 (0.7); 4.2742 (0.6); 4.2698 (0.7); 4.2577 (0.5); 4.2533 (0.7); 4.2480 (0.6); 4.2316 (0.4); 3.3296 (9.6); 2.5214 (0.3); 2.5127 (4.5); 2.5082 (9.2); 2.5036 (12.0); 2.4990 (8.6); 2.4945 (4.2); 2.4830 (0.4); 2.4774 (0.4); 2.4695 (0.5); 2.4647 (0.4); 2.4600 (0.4); 2.4527 (0.6); 2.4422 (16.0); 2.4299 (0.5); 2.4254 (0.4); 2.3358 (0.5); 2.3321 (0.6); 2.3091 (0.7); 2.3057 (0.6); 2.3024 (0.6); 2.2820 (0.4); 2.2790 (0.5); 2.2754 (0.3); 1.2382 (0.4); −0.0002 (1.3) I.022: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.3483 (0.8); 8.3279 (0.9); 8.3148 (8.8); 7.6582 (0.9); 4.2822 (0.4); 4.2763 (0.5); 4.2618 (0.5); 3.3297 (7.8); 3.3058 (1.7); 3.1598 (1.2); 3.1507 (1.4); 3.1445 (1.4); 2.8918 (1.6); 2.7333 (1.3); 2.7321 (1.4); 2.5210 (0.4); 2.5123 (5.5); 2.5079 (11.2); 2.5033 (14.6); 2.4987 (10.4); 2.4942 (4.9); 2.4341 (16.0); 2.0221 (0.5); 2.0094 (0.6); 1.9977 (0.5); 1.8380 (0.6); 1.8274 (0.6); 1.8177 (0.5); 1.8022 (1.4); 1.7893 (0.8); 1.7765 (1.2); 1.7623 (0.5); 1.7545 (0.7); 1.2384 (0.5); −0.0002 (1.6) I.023: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.9530 (0.4); 7.9295 (0.4); 7.2989 (6.3); 5.2638 (1.3); 5.2500 (1.3); 5.2373 (1.3); 5.2235 (1.3); 4.3758 (0.4); 4.3638 (0.6); 4.3519 (0.4); 4.3463 (0.7); 4.3399 (1.8); 4.3226 (1.9); 4.3161 (1.9); 4.2988 (1.9); 4.2923 (0.7); 4.2868 (0.5); 4.2751 (0.6); 4.2630 (0.4); 2.6050 (16.0); 2.5562 (0.5); 2.5422 (0.5); 2.5330 (0.7); 2.5191 (0.7); 2.5099 (0.6); 2.4960 (0.5); 2.0450 (0.4); 1.5899 (10.0); 1.3959 (4.6); 1.3721 (9.4); 1.3483 (4.5); 1.1449 (7.2); 1.1216 (7.0); 1.0559 (7.3); 1.0329 (7.1); 0.0372 (6.0) I.024: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2987 (10.1); 6.8031 (0.8); 6.7146 (1.4); 5.3376 (1.0); 4.2759 (0.4); 4.2624 (0.4); 4.2475 (0.4); 4.2238 (0.4); 4.2116 (1.3); 4.1878 (3.9); 4.1646 (7.5); 4.1497 (4.3); 4.1405 (1.6); 2.8411 (1.1); 2.5975 (16.0); 1.6685 (1.1); 1.6519 (3.1); 1.6412 (3.4); 1.6305 (8.3); 1.3423 (0.3); 1.3267 (0.5); 1.3032 (0.7); 1.2812 (4.4); 1.2675 (1.7); 1.2575 (8.9); 1.2415 (3.5); 1.2338 (4.2); 1.2251 (1.3); 0.0471 (0.4); 0.0362 (13.2); 0.0252 (0.5) I.025: ¹H-NMR(300.2 MHz, MeOD): δ = 8.6853 (0.4); 4.9058 (14.0); 4.0325 (8.0); 3.3541 (4.2); 3.3487 (8.0); 3.3433 (11.1); 3.3380 (8.1); 3.3327 (4.3); 2.6035 (0.4); 2.5485 (16.0); 1.5671 (1.1); 1.5511 (3.0); 1.5401 (3.4); 1.5256 (1.4); 1.3243 (0.4); 1.2027 (1.3); 1.1882 (3.2); 1.1772 (3.2); 1.1612 (1.2) I.026: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.9162 (0.8); 8.3151 (1.0); 4.2741 (8.9); 3.3299 (3.8); 2.5217 (0.3); 2.5130 (4.7); 2.5085 (9.8); 2.5039 (13.0); 2.4993 (9.1); 2.4947 (4.3); 2.4510 (16.0); −0.0002 (1.3) I.027: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.1723 (0.6); 8.3143 (1.9); 3.3372 (15.3); 3.3132 (0.6); 2.5217 (0.4); 2.5129 (6.2); 2.5084 (13.0); 2.5039 (17.1); 2.4993 (12.1); 2.4948 (5.7); 2.4216 (16.0); 1.5730 (1.0); 1.5589 (2.5); 1.5517 (2.5); 1.5385 (1.2); 1.2968 (1.4); 1.2833 (2.5); 1.2763 (2.7); 1.2620 (1.1); −0.0002 (1.4) I.028: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 9.0387 (3.4); 4.7250 (2.8); 4.7055 (2.8); 3.3089 (53.2); 2.8977 (0.9); 2.7386 (0.9); 2.5073 (19.5); 2.4338 (36.1); 2.1925 (0.5); 2.1756 (1.4); 2.1584 (2.3); 2.1400 (2.3); 2.1228 (1.4); 2.1061 (0.5); 1.0840 (15.8); 1.0672 (15.2); 0.9961 (16.0); 0.9794 (15.4) I.029: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.6207 (0.9); 9.6013 (0.9); 7.5476 (1.0); 7.5427 (1.5); 7.5385 (0.5); 7.5290 (1.3); 7.5271 (2.0); 7.5253 (2.5); 7.5237 (2.4); 7.4968 (1.0); 7.4933 (1.4); 7.4880 (0.5); 7.4817 (0.5); 7.4757 (3.0); 7.4714 (1.0); 7.4611 (0.7); 7.4573 (1.5); 7.4440 (0.7); 7.4400 (1.2); 7.4364 (0.6); 7.4294 (0.4); 7.4229 (1.2); 6.3312 (1.4); 6.3118 (1.4); 3.3425 (30.4); 2.8912 (0.5); 2.7330 (0.4); 2.7317 (0.4); 2.5260 (0.4); 2.5213 (0.5); 2.5127 (6.8); 2.5081 (14.1); 2.5035 (18.4); 2.4989 (12.6); 2.4943 (5.6); 2.4426 (0.5); 2.4335 (16.0); 2.4273 (0.5) I.030: ¹H-NMR(400.1 MHz, CDCl3): δ = 8.0206 (0.3); 7.5202 (0.5); 7.4305 (1.4); 7.4124 (3.7); 7.3952 (4.0); 7.3806 (2.4); 7.3652 (2.1); 7.3306 (4.8); 7.3119 (3.6); 7.2606 (57.5); 6.9959 (0.3); 5.8562 (1.1); 5.8367 (1.1); 5.2937 (0.7); 5.2778 (1.3); 5.2568 (1.2); 5.2435 (0.6); 3.2590 (0.8); 3.2455 (0.8); 3.2239 (1.9); 3.2105 (1.8); 3.1818 (1.8); 3.1648 (1.7); 3.1473 (0.8); 3.1301 (0.8); 2.9570 (1.5); 2.8836 (1.4); 2.4284 (16.0); 2.2187 (0.4); 1.6028 (0.4); 1.5462 (43.1); 1.2660 (0.4); 1.2126 (0.5); 1.1952 (0.4); −0.0002 (27.8) I.031: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 10.2933 (1.4); 10.2680 (1.4); 4.8329 (1.5); 4.8121 (1.9); 4.8080 (1.9); 4.7872 (1.5); 3.3517 (1.2); 2.5342 (1.3); 2.5283 (2.8); 2.5223 (4.0); 2.5163 (2.9); 2.5104 (1.4); 2.4488 (0.9); 2.4300 (0.4); 2.3782 (21.8); 2.3445 (0.8); 2.3220 (1.3); 2.3000 (1.3); 2.2777 (0.8); 2.0094 (0.6); 1.9295 (0.5); 1.3753 (0.4); 1.1949 (0.4); 1.1894 (0.4); 1.0574 (8.7); 1.0351 (16.0); 1.0128 (8.2); 0.9796 (0.4); 0.0199 (2.9) I.032: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.8679 (0.9); 8.8507 (0.9); 3.6998 (1.1); 3.6825 (1.2); 3.6759 (1.5); 3.6694 (16.0); 3.6589 (1.2); 3.3365 (34.0); 2.8918 (1.2); 2.7333 (1.0); 2.7321 (1.0); 2.5124 (4.6); 2.5079 (9.4); 2.5033 (12.5); 2.4986 (9.0); 2.4941 (4.2); 2.4190 (15.5); 1.2367 (0.4); 1.2248 (0.3); 1.2163 (0.6); 1.2133 (0.4); 1.2046 (0.6); 1.1961 (0.4); 1.1928 (0.6); 0.6181 (0.5); 0.6088 (0.5); 0.6042 (0.5); 0.5974 (0.5); 0.5942 (0.6); 0.5887 (0.3); 0.5831 (0.4); 0.5732 (0.3); 0.5453 (0.4); 0.5416 (0.4); 0.5318 (0.6); 0.5249 (0.4); 0.5215 (0.5); 0.5114 (0.6); 0.4903 (0.3); 0.4724 (0.4); 0.4624 (0.7); 0.4501 (0.8); 0.4391 (0.6); 0.3875 (0.3); 0.3761 (0.5); 0.3642 (0.7); 0.3518 (0.6); 0.3419 (0.3) I.033: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7888 (1.7); 8.7700 (1.7); 8.1413 (0.4); 8.0782 (3.0); 7.9540 (1.2); 7.0902 (0.4); 7.0644 (3.7); 4.6993 (0.5); 4.6793 (1.2); 4.6658 (1.0); 4.6604 (0.9); 4.6461 (0.5); 3.6500 (15.9); 3.1394 (0.3); 3.1257 (0.4); 3.1022 (2.0); 3.0918 (2.6); 3.0721 (1.8); 3.0558 (0.4); 3.0350 (0.4); 2.8921 (7.0); 2.7331 (6.3); 2.5087 (20.6); 2.5044 (26.0); 2.5000 (19.4); 2.3651 (16.0); 1.2391 (0.7); −0.0002 (2.5) I.034: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6437 (1.2); 8.6251 (1.2); 4.6340 (0.6); 4.6228 (0.8); 4.6164 (1.0); 4.6047 (1.1); 4.5985 (0.7); 4.5873 (0.6); 4.1591 (0.7); 4.1523 (0.8); 4.1413 (2.1); 4.1348 (2.2); 4.1235 (2.2); 4.1171 (2.1); 4.1058 (0.8); 4.0994 (0.6); 3.7465 (0.8); 3.7294 (0.8); 3.7214 (1.8); 3.7044 (1.7); 3.6855 (1.6); 3.6744 (1.8); 3.6604 (0.8); 3.6492 (0.7); 3.3271 (9.2); 3.2786 (18.3); 2.5251 (0.3); 2.5112 (7.5); 2.5071 (14.1); 2.5027 (17.8); 2.4982 (13.1); 2.4177 (16.0); 1.2129 (4.6); 1.1952 (9.4); 1.1774 (4.4); −0.0002 (2.2) I.035: ¹H-NMR(500.1 MHz, d₆-DMSO): δ = 8.6729 (0.8); 8.6580 (0.8); 7.9596 (1.5); 7.4703 (0.6); 4.4037 (0.4); 4.3952 (0.4); 3.6749 (7.8); 3.3203 (16.0); 3.1428 (0.4); 3.1297 (1.0); 3.1173 (1.0); 3.1045 (0.4); 2.8980 (8.4); 2.7386 (7.9); 2.5476 (0.6); 2.5085 (6.0); 2.4291 (7.9); 1.8445 (0.4); 1.7489 (0.4); 1.7312 (0.3); 1.5617 (0.6); 1.5503 (0.7); 1.5319 (0.4) I.036: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 10.8800 (1.4); 8.6138 (1.4); 8.5951 (1.4); 8.3156 (2.0); 7.5388 (1.7); 7.5192 (1.9); 7.3528 (2.1); 7.3327 (2.4); 7.2036 (2.5); 7.1982 (2.4); 7.0914 (0.9); 7.0890 (0.9); 7.0715 (1.8); 7.0539 (1.2); 7.0513 (1.1); 7.0060 (1.3); 7.0038 (1.4); 6.9863 (2.0); 6.9689 (0.9); 6.9666 (0.9); 4.6070 (0.4); 4.5936 (0.6); 4.5882 (0.6); 4.5839 (0.8); 4.5747 (0.7); 4.5707 (0.7); 4.5653 (0.7); 4.5517 (0.5); 4.1222 (1.2); 4.1047 (3.8); 4.0872 (4.0); 4.0695 (1.4); 3.3317 (16.4); 3.3080 (0.6); 3.2954 (0.5); 3.2820 (0.6); 3.2587 (1.3); 3.2456 (1.2); 3.2149 (1.3); 3.1914 (1.2); 3.1785 (0.6); 3.1550 (0.6); 2.5243 (0.5); 2.5195 (0.7); 2.5108 (9.2); 2.5063 (18.7); 2.5018 (24.5); 2.4972 (17.8); 2.4927 (8.7); 2.2591 (16.0); 1.2378 (0.5); 1.1546 (5.4); 1.1368 (11.4); 1.1191 (5.2); −0.0002 (3.4) I.037: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.5752 (0.9); 8.5545 (0.9); 4.8149 (0.4); 4.7967 (0.6); 4.7828 (0.6); 4.7765 (0.5); 4.7627 (0.6); 4.7446 (0.4); 3.4825 (0.4); 3.4690 (0.5); 3.4546 (0.8); 3.4412 (0.8); 3.4248 (0.8); 3.4114 (0.7); 3.3563 (69.9); 3.3339 (1.2); 3.3312 (1.1); 3.3238 (0.8); 3.3061 (0.6); 2.5267 (0.4); 2.5218 (0.6); 2.5133 (7.6); 2.5088 (14.6); 2.5043 (18.9); 2.4997 (13.7); 2.4952 (6.5); 2.4871 (1.0); 2.4840 (0.8); 2.4701 (0.6); 2.4666 (0.5); 2.4560 (0.4); 2.3876 (16.0); 2.3040 (0.3); 2.2911 (0.7); 2.2732 (0.7); 2.2599 (0.6); 2.2420 (0.6); −0.0002 (0.9) I.038: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.3275 (0.4); 8.3148 (0.7); 8.3017 (0.4); 4.0949 (1.3); 4.0772 (4.1); 4.0594 (4.1); 4.0416 (1.3); 3.4721 (0.9); 3.4550 (2.2); 3.4409 (2.2); 3.4240 (1.0); 3.3532 (57.4); 2.5742 (2.0); 2.5571 (4.1); 2.5400 (1.8); 2.5269 (0.4); 2.5221 (0.5); 2.5134 (6.8); 2.5090 (13.5); 2.5045 (17.5); 2.4999 (12.8); 2.4954 (6.2); 2.3519 (16.0); 1.2384 (0.4); 1.1994 (4.6); 1.1817 (9.3); 1.1639 (4.4); −0.0002 (0.7) I.039: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.4000 (1.0); 8.3813 (1.0); 5.1026 (0.8); 5.0879 (1.9); 5.0730 (0.9); 4.4782 (0.5); 4.4653 (1.1); 4.4595 (0.6); 4.4522 (0.6); 4.4466 (1.1); 4.4335 (0.5); 4.1495 (1.0); 4.1319 (3.2); 4.1143 (3.4); 4.0966 (1.1); 3.7872 (1.7); 3.7732 (3.0); 3.7593 (1.7); 3.3474 (55.0); 2.5259 (0.4); 2.5212 (0.6); 2.5125 (7.3); 2.5081 (14.6); 2.5035 (18.9); 2.4989 (13.7); 2.4944 (6.7); 2.3998 (16.0); 1.2388 (0.4); 1.2158 (4.5); 1.1981 (9.2); 1.1803 (4.3); −0.0002 (1.1) I.040: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 10.8822 (1.5); 8.6196 (1.5); 8.6009 (1.5); 7.5394 (1.8); 7.5199 (1.9); 7.3533 (2.1); 7.3332 (2.4); 7.2064 (2.5); 7.2007 (2.6); 7.0900 (0.9); 7.0723 (1.8); 7.0542 (1.1); 7.0524 (1.1); 7.0048 (1.4); 6.9868 (2.0); 6.9679 (0.9); 4.6130 (0.5); 4.5995 (0.7); 4.5943 (0.7); 4.5900 (0.8); 4.5808 (0.7); 4.5765 (0.7); 4.5714 (0.7); 4.5577 (0.5); 4.1238 (1.2); 4.1061 (3.9); 4.0884 (4.0); 4.0707 (1.3); 3.3509 (117.0); 3.3003 (0.6); 3.2869 (0.7); 3.2638 (1.4); 3.2505 (1.2); 3.2215 (1.3); 3.1980 (1.3); 3.1850 (0.6); 3.1617 (0.6); 2.8896 (0.8); 2.7311 (0.7); 2.5251 (0.8); 2.5114 (14.1); 2.5073 (27.7); 2.5028 (36.1); 2.4983 (26.6); 2.4942 (13.4); 2.2175 (16.0); 1.2382 (1.0); 1.1543 (4.8); 1.1366 (10.0); 1.1188 (4.7); −0.0002 (1.4) I.041: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.8530 (1.0); 8.8335 (1.0); 4.5551 (0.4); 4.5451 (0.5); 4.5356 (0.4); 4.5258 (0.7); 4.5180 (0.5); 4.5091 (0.4); 4.4986 (0.4); 3.3305 (29.3); 2.8431 (1.2); 2.8247 (3.8); 2.8062 (3.8); 2.7878 (1.2); 2.5263 (0.5); 2.5216 (0.7); 2.5130 (8.3); 2.5085 (16.8); 2.5039 (22.0); 2.4993 (15.9); 2.4947 (7.7); 2.4052 (16.0); 1.7526 (0.4); 1.7307 (0.5); 1.7250 (0.6); 1.7211 (0.6); 1.7038 (0.3); 1.6942 (0.6); 1.6885 (0.3); 1.6725 (0.4); 1.6664 (0.3); 1.6561 (0.4); 1.6501 (0.4); 1.6399 (0.4); 1.6339 (0.3); 1.6061 (0.7); 1.5949 (0.6); 1.5739 (0.7); 1.5638 (0.4); 1.2375 (0.4); 1.1760 (4.3); 1.1576 (9.2); 1.1391 (4.1); 0.9195 (5.3); 0.9037 (5.0); 0.8784 (4.8); 0.8627 (5.1); −0.0002 (1.7) I.042: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7687 (0.9); 8.7489 (0.9); 7.9526 (0.7); 4.3559 (1.1); 4.3368 (1.5); 4.3187 (1.1); 3.3307 (31.8); 2.8932 (5.6); 2.8649 (1.2); 2.8465 (3.9); 2.8281 (4.0); 2.8097 (1.3); 2.7336 (4.6); 2.5261 (0.5); 2.5213 (0.7); 2.5127 (8.5); 2.5082 (17.1); 2.5036 (22.4); 2.4990 (16.2); 2.4945 (7.9); 2.3872 (16.0); 2.3682 (0.4); 2.2412 (0.5); 2.2241 (1.0); 2.2070 (0.9); 2.1900 (0.6); 1.2398 (0.5); 1.1829 (4.4); 1.1645 (9.3); 1.1461 (4.2); 1.1002 (0.4); 1.0831 (0.3); 0.9566 (6.6); 0.9519 (6.5); 0.9397 (6.5); 0.9349 (6.2); −0.0002 (1.6) I.043: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7995 (0.9); 8.7804 (0.9); 6.3319 (0.4); 6.2030 (0.4); 6.1918 (0.9); 6.1803 (0.4); 6.0518 (0.4); 4.6373 (0.3); 4.6230 (0.4); 4.6177 (0.7); 4.6032 (0.6); 4.5829 (0.3); 3.6825 (15.3); 3.3472 (48.5); 2.5260 (0.4); 2.5213 (0.6); 2.5127 (7.2); 2.5082 (14.5); 2.5036 (18.9); 2.4990 (13.6); 2.4945 (6.6); 2.4592 (0.4); 2.4559 (0.4); 2.4455 (0.3); 2.4302 (0.5); 2.4182 (0.9); 2.4070 (0.6); 2.3917 (16.0); 2.3751 (0.4); 2.3704 (0.4); 2.3593 (0.3); 1.2391 (0.3); −0.0002 (1.0) I.044: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6515 (0.9); 8.6328 (0.9); 4.6420 (0.5); 4.6309 (0.6); 4.6244 (0.8); 4.6127 (0.9); 4.6064 (0.6); 4.5952 (0.5); 4.1613 (0.6); 4.1545 (0.7); 4.1435 (1.9); 4.1369 (2.0); 4.1257 (2.0); 4.1192 (1.9); 4.1080 (0.7); 4.1015 (0.6); 3.7532 (0.8); 3.7361 (0.7); 3.7280 (1.6); 3.7110 (1.5); 3.6911 (1.5); 3.6800 (1.6); 3.6659 (0.8); 3.6548 (0.7); 3.3492 (71.7); 3.2802 (18.0); 2.5261 (0.4); 2.5214 (0.6); 2.5127 (7.5); 2.5083 (15.1); 2.5037 (19.7); 2.4991 (14.3); 2.4945 (6.9); 2.3803 (16.0); 1.2133 (4.4); 1.1956 (9.2); 1.1778 (4.3); −0.0002 (0.8) I.045: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.5188 (0.4); 7.3255 (1.5); 7.3060 (1.5); 7.2608 (64.2); 6.9946 (0.4); 5.5392 (0.9); 5.3300 (0.9); 4.9552 (0.8); 4.9465 (1.5); 4.9360 (1.5); 4.9268 (1.4); 4.9152 (0.8); 4.2831 (1.4); 4.2670 (4.0); 4.2487 (4.1); 4.2313 (1.4); 3.1060 (1.2); 3.0982 (1.2); 3.0662 (1.7); 3.0564 (1.6); 2.8818 (1.7); 2.8707 (1.6); 2.8401 (1.2); 2.8301 (1.1); 2.5095 (16.0); 1.5469 (68.3); 1.3102 (4.3); 1.2923 (8.2); 1.2743 (4.2); −0.0002 (31.2) I.046: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.7493 (2.1); 8.7320 (2.2); 7.3516 (1.9); 6.8518 (2.0); 4.3909 (0.7); 4.3598 (1.4); 4.3386 (0.8); 3.6588 (15.8); 3.3098 (4.3); 2.5001 (5.9); 2.3962 (16.0); 2.2244 (2.0); 2.2065 (4.7); 2.1889 (3.0); 2.0991 (0.4); 2.0822 (0.7); 2.0660 (1.0); 2.0482 (1.3); 2.0342 (1.0); 2.0159 (0.4); 1.9884 (0.5); 1.9532 (0.5); 1.9357 (1.0); 1.9163 (1.2); 1.8992 (1.0); 1.8812 (0.7); −0.0002 (3.4) I.047: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2614 (8.9); 6.5045 (1.8); 4.3018 (1.4); 4.2840 (4.1); 4.2662 (4.1); 4.2484 (1.4); 2.6604 (4.4); 2.6398 (7.1); 2.6201 (3.9); 2.4838 (16.0); 2.1597 (0.7); 2.1398 (2.1); 2.1195 (2.9); 2.0995 (1.8); 2.0788 (0.5); 1.5543 (10.4); 1.3341 (4.2); 1.3163 (8.2); 1.2986 (4.0); −0.0002 (4.4) I.048: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 12.3893 (0.6); 8.3998 (2.9); 8.3939 (3.0); 8.3799 (3.2); 7.2539 (1.3); 7.2356 (3.6); 7.2223 (7.1); 7.2123 (9.3); 7.1970 (3.5); 4.7638 (0.7); 4.7433 (1.4); 4.7314 (1.3); 4.7109 (0.7); 4.4869 (0.7); 4.4669 (1.4); 4.4524 (1.4); 4.4336 (0.7); 3.5942 (16.0); 3.3169 (4.0); 3.0532 (0.8); 3.0390 (0.9); 3.0183 (1.9); 3.0047 (1.7); 2.9809 (1.8); 2.9593 (1.7); 2.9468 (0.9); 2.9248 (0.8); 2.8895 (1.5); 2.7534 (0.9); 2.7411 (1.1); 2.7306 (1.6); 2.7116 (1.8); 2.6999 (1.6); 2.6403 (1.6); 2.6184 (1.6); 2.5987 (0.9); 2.5769 (0.9); 2.5008 (7.0); 2.4533 (1.1); 2.3270 (15.1); −0.0002 (0.8) I.049: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2984 (4.6); 6.4029 (1.0); 2.9518 (1.2); 2.9269 (3.7); 2.9021 (3.8); 2.8774 (1.3); 2.5606 (16.0); 1.8328 (1.1); 1.8162 (3.0); 1.8047 (3.1); 1.7894 (1.3); 1.6033 (7.1); 1.4014 (1.3); 1.3861 (3.2); 1.3745 (3.1); 1.3578 (1.1); 1.2969 (4.0); 1.2721 (8.1); 1.2473 (3.7); 0.0357 (4.6) I.050: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.7225 (0.6); 7.2985 (2.3); 3.7614 (16.0); 2.4791 (13.4); 1.8417 (1.0); 1.8240 (2.8); 1.8137 (2.7); 1.7972 (1.2); 1.4371 (1.2); 1.4207 (2.7); 1.4103 (2.8); 1.3926 (1.0); 0.0354 (2.4) I.051: ¹H-NMR(499.9 MHz, CDCl3): δ = 7.2608 (13.1); 6.5280 (0.7); 6.5135 (0.8); 5.8808 (0.5); 5.5378 (0.6); 4.4926 (0.9); 4.4806 (1.3); 4.4763 (1.2); 4.4643 (1.1); 4.0276 (0.7); 3.4834 (0.6); 3.4753 (0.6); 3.4677 (0.6); 2.9566 (0.8); 2.8838 (0.7); 2.5538 (16.0); 2.2227 (0.3); 2.2095 (0.7); 2.1962 (1.1); 2.1833 (1.2); 2.1699 (0.8); 1.9497 (1.3); 1.9437 (1.4); 1.9250 (1.5); 1.7095 (1.4); 1.7019 (1.2); 1.6893 (1.3); 1.6822 (1.6); 1.6120 (0.8); 1.6042 (0.7); 1.5774 (4.0); 1.5640 (1.6); 1.3926 (0.4); 1.3862 (0.6); 1.3787 (0.5); 1.3625 (1.4); 1.3361 (1.5); 1.3184 (0.7); 1.3116 (0.8); 1.3054 (0.6); 1.2549 (1.5); 1.1940 (0.4); 1.1872 (0.5); 1.1803 (0.4); 1.1632 (0.9); 1.1561 (0.7); 1.1374 (1.0); 1.1334 (1.1); 1.1081 (1.6); 1.0867 (1.4); 1.0819 (1.4); 1.0628 (0.8); 1.0433 (7.6); 1.0294 (10.4); 1.0272 (9.8); 1.0131 (7.4); 0.8800 (0.5); 0.8719 (0.4); 0.8607 (0.4); −0.0002 (14.5) I.052: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 11.3169 (0.5); 8.7860 (0.4); 8.7667 (0.4); 8.6199 (1.4); 8.6007 (1.4); 7.4620 (1.2); 7.0086 (1.2); 4.7521 (0.5); 4.7338 (1.2); 4.7195 (1.1); 4.7152 (0.8); 4.7010 (0.5); 3.6440 (15.5); 3.3283 (6.4); 2.9423 (0.3); 2.9218 (0.4); 2.8984 (0.4); 2.8923 (0.5); 2.7336 (0.4); 2.7157 (0.6); 2.7019 (0.7); 2.6766 (1.7); 2.6629 (1.5); 2.6393 (1.8); 2.6213 (1.7); 2.6003 (0.6); 2.5940 (0.4); 2.5817 (0.8); 2.5122 (5.8); 2.5082 (11.2); 2.5038 (14.2); 2.4993 (10.3); 2.4346 (5.3); 2.4167 (16.0); 1.2388 (0.6); 0.0079 (0.3); −0.0002 (8.7); −0.0085 (0.3) I.053: ¹H-NMR(500.1 MHz, d₆-DMSO): δ = 8.6109 (1.2); 8.5956 (1.2); 7.4540 (0.9); 6.9983 (0.9); 4.7503 (0.5); 4.7392 (0.6); 4.7355 (1.0); 4.7242 (1.0); 4.7204 (0.7); 4.7093 (0.5); 3.6464 (16.0); 3.3242 (0.4); 2.7111 (0.6); 2.7000 (0.7); 2.6798 (1.5); 2.6688 (1.4); 2.6380 (1.4); 2.6232 (1.6); 2.6067 (0.7); 2.5920 (0.7); 2.5127 (0.7); 2.5091 (1.6); 2.5054 (2.3); 2.5018 (1.7); 2.4981 (0.8); 2.4374 (1.5); 2.4197 (16.4) I.054: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6271 (1.1); 8.6079 (1.1); 7.4719 (0.9); 7.0149 (0.9); 4.7596 (0.5); 4.7456 (0.6); 4.7412 (1.0); 4.7270 (1.0); 4.7224 (0.7); 4.7084 (0.5); 3.6456 (15.0); 3.3300 (12.0); 2.8921 (0.4); 2.7221 (0.6); 2.7083 (0.6); 2.6830 (1.6); 2.6692 (1.4); 2.6486 (1.4); 2.6417 (0.4); 2.6303 (1.5); 2.6094 (0.6); 2.5913 (0.6); 2.5126 (4.8); 2.5081 (9.6); 2.5036 (12.6); 2.4990 (9.0); 2.4944 (4.3); 2.3942 (3.2); 2.3778 (16.0); 1.2390 (0.4); −0.0002 (7.2) I.055: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.6185 (1.4); 8.5994 (1.4); 7.4602 (1.1); 7.0011 (1.1); 4.7581 (0.5); 4.7398 (1.1); 4.7255 (1.1); 4.7212 (0.8); 4.7070 (0.6); 4.0384 (0.8); 4.0206 (0.8); 3.6436 (15.2); 3.3120 (9.7); 2.7196 (0.6); 2.7058 (0.6); 2.6897 (8.8); 2.6806 (1.9); 2.6667 (1.6); 2.6458 (1.6); 2.6276 (1.6); 2.6067 (0.6); 2.5885 (0.6); 2.5053 (3.9); 2.5009 (5.3); 2.4965 (4.0); 2.3767 (16.0); 1.9881 (3.3); 1.1926 (0.9); 1.1748 (1.8); 1.1570 (0.9); −0.0002 (5.8); −0.0082 (0.4) I.056: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2984 (1.1); 4.2985 (1.2); 4.2746 (3.8); 4.2508 (4.1); 4.2270 (2.6); 3.1169 (16.0); 2.3313 (5.9); 1.3536 (4.3); 1.3298 (8.6); 1.3059 (4.2); 0.0257 (0.9) I.057: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2984 (1.4); 4.3034 (1.2); 4.2795 (3.8); 4.2557 (4.0); 4.2317 (2.9); 3.1271 (16.0); 2.2833 (7.0); 1.6659 (0.6); 1.3580 (4.1); 1.3342 (8.4); 1.3104 (4.1); 0.0295 (1.6) I.058: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2981 (1.1); 4.2827 (1.3); 4.2589 (4.2); 4.2351 (4.4); 4.2113 (1.5); 3.0357 (10.8); 2.3654 (0.5); 2.3433 (0.7); 2.3304 (0.6); 2.3212 (0.6); 2.3085 (0.7); 2.2992 (0.3); 2.2862 (0.6); 2.2636 (16.0); 1.3512 (4.8); 1.3274 (9.8); 1.3037 (4.7); 1.0552 (1.8); 1.0360 (1.8); 0.9905 (4.6); 0.9680 (4.3); 0.0261 (1.0) I.059: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2982 (1.6); 4.2875 (1.3); 4.2637 (4.2); 4.2399 (4.4); 4.2161 (1.5); 3.0444 (14.1); 2.3701 (0.5); 2.3479 (0.7); 2.3352 (0.5); 2.3258 (0.6); 2.3131 (0.7); 2.2910 (0.5); 2.2147 (16.0); 1.3553 (4.7); 1.3316 (9.4); 1.3078 (4.5); 1.0606 (2.0); 1.0397 (2.0); 0.9941 (4.7); 0.9717 (4.4); 0.0297 (1.6) I.060: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 10.5395 (1.0); 3.4341 (16.0); 2.5342 (1.1); 2.5282 (2.3); 2.5222 (3.2); 2.5161 (2.2); 2.5102 (1.1); 2.3102 (11.8); 2.0877 (0.4); 1.5654 (0.7); 1.5483 (1.8); 1.5374 (2.0); 1.5227 (0.9); 1.3143 (0.9); 1.2998 (1.9); 1.2889 (1.8); 1.2718 (0.7); 0.0151 (2.8) I.061: ¹H-NMR(499.9 MHz, d₆-DMSO): δ = 8.3820 (1.7); 8.3664 (1.6); 4.7123 (1.0); 3.7834 (9.0); 3.7272 (0.4); 3.7042 (1.3); 3.5118 (0.3); 3.3971 (0.6); 3.3141 (79.4); 3.2713 (0.5); 3.2643 (0.4); 3.2548 (1.3); 3.1485 (6.3); 2.8939 (1.2); 2.7343 (1.2); 2.6391 (0.8); 2.5078 (38.0); 2.5043 (51.2); 2.5008 (37.5); 2.4060 (37.6); 2.3652 (0.4); 2.1189 (0.5); 2.1052 (1.3); 2.0913 (1.9); 2.0761 (2.0); 2.0622 (1.3); 2.0488 (0.5); 1.0358 (0.4); 1.0224 (0.4); 0.9556 (16.0); 0.9422 (15.5); 0.9124 (14.5); 0.8988 (14.0) I.062: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 8.3298 (1.1); 8.3107 (2.2); 8.2915 (1.1); 7.4419 (1.9); 7.0971 (1.9); 3.8134 (8.2); 3.7938 (8.2); 3.3523 (16.0); 2.9101 (2.0); 2.7514 (1.7); 2.7498 (1.6); 2.5340 (1.2); 2.5281 (2.6); 2.5220 (3.5); 2.5159 (2.5); 2.5100 (1.2); 2.4326 (35.4); 0.0181 (1.4) I.063: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 8.6245 (2.4); 7.3264 (0.7); 7.0720 (0.7); 3.3471 (16.0); 2.9110 (1.0); 2.7519 (0.8); 2.7502 (0.8); 2.5342 (1.2); 2.5282 (2.7); 2.5221 (3.7); 2.5160 (2.7); 2.5100 (1.3); 2.3931 (17.2); 1.3490 (1.1); 1.3339 (2.7); 1.3229 (3.0); 1.3093 (1.3); 0.9978 (1.3); 0.9842 (3.0); 0.9732 (2.8); 0.9581 (1.1); 0.0198 (3.9) I.064: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.4560 (1.2); 8.4350 (1.2); 7.9528 (0.5); 7.8767 (1.5); 4.4939 (0.4); 4.4723 (0.9); 4.4681 (0.7); 4.4506 (0.6); 4.4465 (0.9); 4.4249 (0.4); 3.3251 (15.5); 3.2308 (1.4); 3.2244 (1.0); 3.2213 (1.0); 3.2183 (1.1); 3.2078 (1.6); 3.1949 (1.0); 2.8914 (4.1); 2.7323 (3.3); 2.5249 (0.4); 2.5201 (0.6); 2.5115 (8.3); 2.5071 (16.9); 2.5025 (22.1); 2.4979 (15.8); 2.4934 (7.5); 2.4283 (16.0); 2.3577 (0.3); 2.3491 (0.4); 2.3401 (0.5); 2.3351 (0.5); 2.3278 (0.7); 2.3189 (0.5); 2.3055 (0.3); 2.0091 (0.7); 2.0022 (0.4); 1.9830 (0.7); 1.9791 (0.7); 1.9596 (0.4); 1.9527 (0.6); 1.2395 (0.5); −0.0002 (3.3) I.065: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6188 (1.2); 8.6023 (1.2); 7.9535 (0.4); 7.6652 (1.5); 4.5476 (0.4); 4.5440 (0.4); 4.5296 (0.7); 4.5198 (0.6); 4.5124 (0.7); 4.4980 (0.4); 3.5835 (1.0); 3.5649 (1.2); 3.5585 (1.2); 3.5399 (1.0); 3.3272 (9.4); 3.1483 (1.2); 3.1371 (1.1); 3.1232 (1.0); 3.1120 (1.0); 2.8921 (2.6); 2.7330 (2.4); 2.5371 (1.2); 2.5118 (9.3); 2.5076 (15.3); 2.5032 (18.1); 2.4987 (12.7); 2.4735 (1.4); 2.4009 (16.0); 2.2268 (1.5); 2.2130 (1.4); 2.1847 (1.1); 2.1710 (1.1); 1.2392 (0.4); −0.0002 (2.1) I.066: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.3150 (1.2); 8.2973 (1.2); 7.5680 (1.1); 4.1417 (0.4); 4.1335 (0.4); 4.1253 (0.5); 4.1177 (0.5); 4.1091 (0.4); 4.1007 (0.4); 3.3292 (8.7); 3.1952 (0.5); 3.1819 (1.1); 3.1777 (1.1); 3.1713 (1.1); 3.1599 (0.7); 3.1473 (0.6); 2.5126 (4.3); 2.5082 (9.0); 2.5037 (12.0); 2.4991 (8.9); 2.4946 (4.4); 2.4763 (0.6); 2.4733 (0.6); 2.4616 (0.6); 2.4587 (0.6); 2.4304 (0.8); 2.4187 (0.8); 2.4157 (0.8); 2.3982 (16.0); 2.2523 (1.2); 2.2296 (1.1); 2.2093 (0.8); 2.1865 (0.8); 1.9519 (0.4); 1.9410 (0.4); 1.9287 (0.4); 1.9192 (0.5); 1.9091 (0.5); 1.7165 (0.4); 1.7079 (0.3); 1.7017 (0.5); 1.6925 (0.4); 1.6842 (0.4); 1.6775 (0.3); 1.6693 (0.3); 1.2381 (0.3); −0.0002 (1.9) I.067: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.1864 (1.1); 8.1673 (1.1); 7.9531 (2.1); 4.4213 (0.4); 4.4091 (1.0); 4.4023 (0.6); 4.3963 (0.6); 4.3901 (1.1); 4.3773 (0.5); 3.7790 (3.1); 3.7663 (3.3); 2.8920 (14.4); 2.7333 (12.3); 2.7322 (11.8); 2.5497 (0.9); 2.5126 (4.6); 2.5082 (9.6); 2.5036 (12.7); 2.4990 (9.3); 2.4945 (4.6); 2.4108 (16.0); 2.3925 (0.4); −0.0002 (8.0); −0.0085 (0.3) I.068: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.4890 (1.2); 8.4694 (1.2); 7.4618 (0.9); 6.9978 (1.0); 4.6730 (0.4); 4.6592 (0.6); 4.6549 (0.9); 4.6405 (0.8); 4.6358 (0.6); 4.6221 (0.4); 2.8917 (0.3); 2.7003 (0.4); 2.6867 (0.5); 2.6612 (1.4); 2.6477 (1.3); 2.6389 (1.3); 2.6209 (1.3); 2.5998 (0.4); 2.5819 (0.4); 2.5128 (4.4); 2.5083 (9.2); 2.5037 (12.1); 2.4991 (8.6); 2.4946 (4.0); 2.3854 (16.0); −0.0002 (8.3) I.069: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.6035 (2.4); 8.5860 (2.4); 7.9605 (3.7); 7.3592 (2.3); 6.8423 (2.4); 4.2936 (1.7); 3.3294 (63.1); 2.8996 (16.0); 2.7404 (15.2); 2.5646 (0.4); 2.5099 (14.0); 2.4098 (16.9); 2.2332 (2.4); 2.2157 (5.3); 2.1987 (3.3); 2.0783 (1.3); 2.0604 (1.5); 2.0481 (1.2); 1.9552 (0.6); 1.9388 (1.2); 1.9200 (1.4); 1.9023 (1.2); 1.8838 (0.8) I.070: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 10.8555 (1.5); 8.4190 (1.4); 8.3996 (1.5); 7.9522 (2.2); 7.5687 (1.6); 7.5492 (1.8); 7.3466 (2.0); 7.3264 (2.3); 7.1909 (2.4); 7.1852 (2.4); 7.0850 (0.8); 7.0825 (0.9); 7.0650 (1.8); 7.0474 (1.1); 7.0448 (1.1); 6.9972 (1.2); 6.9951 (1.3); 6.9775 (1.9); 6.9601 (0.9); 6.9579 (0.9); 4.6043 (0.4); 4.5931 (0.5); 4.5805 (0.7); 4.5736 (0.7); 4.5695 (0.6); 4.5610 (0.6); 4.5495 (0.5); 3.3254 (0.9); 3.3140 (0.9); 3.2887 (1.2); 3.2776 (1.1); 3.2076 (1.1); 3.1831 (1.1); 3.1710 (0.7); 3.1466 (0.6); 2.8887 (16.0); 2.7311 (13.1); 2.5450 (0.5); 2.5196 (0.5); 2.5110 (6.8); 2.5065 (14.2); 2.5019 (19.1); 2.4974 (14.0); 2.4929 (6.9); 2.4508 (1.0); 2.1985 (15.2); 1.2385 (0.4); 0.0081 (0.4); −0.0002 (12.5); −0.0084 (0.5) I.071: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.1866 (1.2); 8.1676 (1.2); 7.9529 (2.3); 4.4156 (0.4); 4.4033 (0.9); 4.3966 (0.6); 4.3908 (0.6); 4.3845 (1.0); 4.3719 (0.4); 3.7734 (3.2); 3.7608 (3.2); 2.8921 (16.0); 2.7334 (13.6); 2.7325 (13.1); 2.5494 (1.1); 2.5126 (5.4); 2.5082 (11.0); 2.5036 (14.5); 2.4990 (10.5); 2.4945 (5.2); 2.4485 (15.9); 2.4305 (0.4); −0.0002 (9.2); −0.0085 (0.4) I.072: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.5947 (3.2); 8.5773 (3.1); 7.9603 (3.7); 7.3535 (3.0); 6.8376 (3.0); 4.2887 (2.2); 3.5552 (0.5); 3.3314 (66.0); 3.0681 (0.4); 2.8992 (16.0); 2.7401 (15.2); 2.5100 (16.5); 2.4462 (21.5); 2.2294 (3.1); 2.2116 (6.7); 2.1945 (4.2); 2.0884 (1.1); 2.0717 (1.6); 2.0543 (1.8); 2.0421 (1.5); 1.9481 (0.8); 1.9302 (1.6); 1.9112 (1.8); 1.8964 (1.5); 1.8756 (1.0); 1.8563 (0.4) I.073: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 10.8446 (2.4); 8.3993 (1.7); 8.3817 (1.7); 7.9606 (3.8); 7.5722 (1.9); 7.5523 (2.0); 7.3536 (2.0); 7.3329 (2.2); 7.1883 (3.4); 7.0902 (1.0); 7.0735 (2.0); 7.0542 (1.3); 7.0022 (1.4); 6.9842 (2.0); 6.9668 (0.9); 4.5769 (1.3); 3.3302 (87.9); 3.2054 (1.8); 3.1806 (1.7); 3.1451 (1.0); 2.8983 (16.0); 2.7398 (15.2); 2.5102 (13.6); 2.2471 (11.1) I.074: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 11.4082 (1.5); 8.3821 (0.5); 8.3542 (0.6); 3.9988 (0.4); 3.9706 (0.8); 3.9425 (0.4); 3.6154 (7.0); 3.3457 (16.0); 2.5337 (1.4); 2.5279 (2.8); 2.5219 (3.8); 2.5159 (2.8); 2.5101 (1.3); 2.4142 (7.0); 0.9432 (2.7); 0.9248 (3.4); 0.9218 (3.4); 0.9036 (2.4); 0.0196 (1.6) I.075: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 8.8853 (0.7); 8.8668 (1.4); 8.8482 (0.7); 8.3626 (1.3); 8.3350 (1.4); 4.2802 (0.4); 4.2615 (0.4); 4.2311 (1.2); 4.2221 (2.1); 4.2034 (4.6); 4.1820 (2.3); 4.1427 (0.4); 4.1241 (0.3); 3.3500 (16.0); 2.5339 (1.1); 2.5280 (2.4); 2.5220 (3.2); 2.5160 (2.3); 2.5103 (1.1); 2.4272 (16.7); 2.1449 (0.5); 2.1221 (0.8); 2.0974 (0.8); 2.0745 (0.5); 0.9479 (6.2); 0.9337 (6.5); 0.9257 (6.8); 0.9114 (5.4); 0.0185 (1.5) I.076: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 8.5202 (0.6); 8.4939 (0.6); 7.4707 (0.5); 7.0219 (0.5); 4.6723 (0.4); 4.6534 (0.4); 3.3550 (16.0); 2.6728 (0.6); 2.6540 (0.7); 2.6496 (0.7); 2.6244 (0.6); 2.5281 (3.8); 2.5221 (5.0); 2.5162 (3.6); 2.4403 (6.0); 0.0195 (3.0) I.077: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 9.5421 (4.4); 9.5247 (4.3); 7.9607 (1.0); 5.9151 (5.3); 5.8973 (5.1); 4.2689 (2.8); 4.2517 (7.5); 4.2342 (7.5); 4.2171 (2.8); 3.3141 (123.1); 2.8995 (4.5); 2.7405 (4.3); 2.5102 (22.1); 2.4671 (30.0); 1.2924 (0.5); 1.2548 (8.6); 1.2374 (16.0); 1.2199 (8.0) I.078: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.6970 (2.0); 8.6782 (2.0); 7.9603 (0.6); 4.7764 (0.7); 4.7591 (1.7); 4.7422 (1.7); 4.7244 (0.7); 3.6660 (16.0); 3.3157 (14.1); 2.8996 (3.0); 2.8773 (1.0); 2.8488 (1.9); 2.8357 (1.8); 2.7681 (1.8); 2.7415 (3.2); 2.7280 (1.0); 2.7075 (0.9); 2.5104 (10.3); 2.3797 (16.0) I.079: ¹H-NMR(500.1 MHz, d₆-DMSO): δ = 8.6757 (1.1); 8.6607 (1.1); 7.9596 (1.5); 7.4627 (0.5); 7.4523 (0.9); 7.4415 (0.5); 4.4285 (0.3); 4.4109 (0.6); 4.4016 (0.5); 4.3959 (0.5); 4.3845 (0.3); 3.6774 (9.2); 3.3224 (16.0); 3.1460 (0.5); 3.1328 (1.3); 3.1201 (1.3); 3.1067 (0.5); 2.8981 (8.1); 2.7387 (7.7); 2.5477 (0.7); 2.5091 (6.8); 2.3928 (9.4); 1.8646 (0.3); 1.8506 (0.5); 1.8401 (0.3); 1.7659 (0.4); 1.7541 (0.4); 1.7470 (0.4); 1.7363 (0.4); 1.5628 (0.7); 1.5523 (0.8); 1.5332 (0.5) I.080: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 12.9252 (0.3); 12.7164 (0.8); 12.6792 (0.8); 12.6348 (0.8); 12.5656 (0.6); 12.5139 (0.5); 8.7163 (15.8); 8.6924 (16.0); 3.9736 (0.4); 3.9467 (0.4); 3.8009 (0.3); 3.6872 (13.0); 3.6632 (14.7); 3.6567 (15.4); 3.6326 (13.4); 3.5661 (0.6); 3.3623 (2.5); 3.1879 (14.4); 3.1214 (0.5); 2.6544 (1.0); 2.5340 (10.3); 2.5281 (21.5); 2.5221 (29.4); 2.5161 (21.7); 2.5101 (10.9); 2.4402 (194.0); 2.3735 (1.5); 2.2927 (0.3); 2.2222 (1.0); 2.0952 (2.8); 1.2752 (1.4); 1.2588 (3.2); 1.2441 (4.2); 1.2319 (7.0); 1.2168 (6.8); 1.2020 (7.2); 1.1859 (4.4); 1.1750 (3.8); 1.1588 (2.0); 1.0747 (0.4); 0.6700 (0.7); 0.6451 (4.6); 0.6387 (4.0); 0.6285 (6.8); 0.6101 (9.3); 0.5993 (9.2); 0.5821 (5.6); 0.5717 (4.6); 0.5539 (4.0); 0.5364 (6.3); 0.5250 (9.0); 0.5081 (14.3); 0.5005 (14.4); 0.4831 (15.5); 0.4666 (11.1); 0.4544 (8.4); 0.4376 (3.8); 0.4143 (1.2); 0.3974 (4.9); 0.3918 (4.6); 0.3855 (6.2); 0.3817 (6.2); 0.3684 (10.4); 0.3511 (9.4); 0.3416 (5.7); 0.3340 (3.6); 0.3113 (1.2); 0.0294 (1.3); 0.0186 (31.4); 0.0076 (1.4) I.081: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2603 (6.5); 6.3141 (1.1); 6.2984 (1.1); 4.2308 (1.4); 4.2108 (2.6); 4.1914 (1.3); 3.8021 (16.0); 2.4928 (15.7); 1.5427 (4.8); 1.1754 (0.7); 1.1630 (1.2); 1.1432 (1.2); 1.1341 (0.7); 0.6700 (0.6); 0.6553 (1.0); 0.6384 (1.6); 0.6182 (1.5); 0.5996 (1.2); 0.5805 (1.6); 0.5626 (1.7); 0.5485 (1.6); 0.5372 (1.4); 0.5182 (0.9); 0.4985 (1.4); 0.4840 (1.2); −0.0002 (8.5) I.082: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.5237 (1.8); 3.5926 (16.0); 3.3265 (10.0); 2.8919 (0.3); 2.6244 (7.0); 2.5251 (0.4); 2.5116 (7.4); 2.5074 (14.7); 2.5029 (19.3); 2.4984 (14.4); 2.4941 (7.3); 2.3146 (15.9); 0.8433 (0.4); 0.8182 (3.2); 0.8139 (2.4); 0.8007 (2.3); 0.7961 (3.2); 0.7707 (0.4); −0.0002 (4.6) I.083: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.8726 (1.3); 8.8556 (1.3); 4.1791 (0.6); 4.1699 (0.6); 4.1613 (0.7); 4.1521 (1.8); 4.1469 (0.8); 4.1343 (2.0); 4.1292 (1.9); 4.1163 (0.8); 4.1115 (1.8); 4.1021 (0.6); 4.0938 (0.6); 4.0844 (0.6); 3.6662 (1.2); 3.6491 (1.4); 3.6427 (1.4); 3.6255 (1.3); 3.3392 (27.2); 2.5082 (11.8); 2.5039 (14.5); 2.4996 (10.6); 2.3823 (16.0); 1.2347 (0.6); 1.2214 (4.9); 1.2138 (1.3); 1.2035 (9.8); 1.1858 (4.7); 1.1710 (0.4); 0.6315 (0.3); 0.6281 (0.4); 0.6198 (0.8); 0.6109 (0.8); 0.6066 (0.8); 0.5967 (0.8); 0.5853 (0.5); 0.5755 (0.4); 0.5583 (0.4); 0.5450 (0.6); 0.5355 (0.8); 0.5246 (0.8); 0.5147 (0.9); 0.5027 (0.4); 0.4939 (0.8); 0.4808 (0.6); 0.4711 (0.9); 0.4590 (1.1); 0.4478 (0.8); 0.4354 (0.3); 0.3956 (0.5); 0.3846 (0.8); 0.3728 (1.0); 0.3604 (0.9); 0.3502 (0.5) I.084: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.1947 (0.5); 9.1765 (0.5); 5.3033 (1.1); 5.2850 (1.1); 3.7384 (16.0); 3.3304 (5.7); 2.5203 (0.3); 2.5116 (4.0); 2.5071 (8.0); 2.5026 (10.4); 2.4980 (7.6); 2.4935 (3.7); 2.4029 (9.0); −0.0002 (2.8) I.085: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6528 (1.0); 8.6343 (1.1); 4.4143 (0.5); 4.4008 (0.6); 4.3956 (0.6); 4.3919 (0.6); 4.3822 (0.7); 4.3784 (0.6); 4.3733 (0.6); 4.3598 (0.5); 4.1415 (0.6); 4.1371 (0.7); 4.1237 (2.1); 4.1194 (2.2); 4.1059 (2.2); 4.1017 (2.1); 4.0923 (0.3); 4.0881 (0.8); 4.0841 (0.7); 3.3267 (15.0); 2.8919 (2.1); 2.7329 (1.7); 2.5252 (0.4); 2.5203 (0.6); 2.5117 (8.3); 2.5073 (16.7); 2.5027 (21.8); 2.4981 (16.0); 2.4937 (7.8); 2.3872 (16.0); 1.7820 (0.3); 1.7650 (0.4); 1.7596 (0.4); 1.7469 (0.6); 1.7301 (0.6); 1.7247 (0.6); 1.7077 (0.6); 1.6545 (0.5); 1.6408 (0.7); 1.6366 (0.7); 1.6225 (0.7); 1.6058 (0.4); 1.6015 (0.4); 1.5878 (0.4); 1.2130 (4.4); 1.1952 (9.3); 1.1775 (4.4); 0.8224 (0.4); 0.8160 (0.4); 0.8039 (0.6); 0.7917 (0.4); 0.7854 (0.4); 0.4591 (0.5); 0.4500 (0.6); 0.4466 (0.6); 0.4391 (1.1); 0.4300 (1.0); 0.4272 (1.0); 0.4186 (1.2); 0.4081 (0.7); 0.3983 (0.5); 0.1932 (0.5); 0.1840 (0.5); 0.1803 (0.6); 0.1699 (0.6); 0.1620 (0.5); 0.1582 (0.4); 0.0760 (0.4); 0.0724 (0.6); 0.0639 (0.7); 0.0536 (0.6); 0.0508 (0.6); 0.0411 (0.5); −0.0002 (6.1) I.086: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.2911 (1.9); 3.5853 (15.8); 3.3258 (15.0); 2.5246 (0.4); 2.5199 (0.6); 2.5111 (8.2); 2.5066 (16.7); 2.5021 (22.2); 2.4975 (16.4); 2.4930 (8.2); 2.3362 (16.0); 1.3268 (0.4); 1.3131 (1.0); 1.3056 (1.0); 1.2995 (0.7); 1.2920 (2.0); 1.2844 (0.7); 1.2782 (1.1); 1.2708 (1.1); 1.2570 (0.5); 0.5426 (0.3); 0.5372 (0.6); 0.5328 (0.6); 0.5280 (0.8); 0.5236 (0.7); 0.5187 (0.7); 0.5139 (1.3); 0.5088 (1.1); 0.5003 (0.8); 0.4950 (0.9); 0.4847 (0.3); 0.4708 (0.5); 0.4450 (2.5); 0.4410 (2.6); 0.4352 (1.4); 0.4238 (2.4); 0.4197 (2.8); 0.4143 (1.5); 0.3958 (0.6); 0.3819 (0.4); 0.3712 (1.0); 0.3668 (0.9); 0.3576 (1.0); 0.3529 (1.3); 0.3473 (0.7); 0.3434 (0.7); 0.3392 (0.8); 0.3336 (0.7); 0.3298 (0.6); 0.3239 (0.4); −0.0002 (5.5) I.087: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.1628 (1.1); 9.1444 (1.0); 5.2291 (2.2); 5.2108 (2.2); 4.2479 (0.8); 4.2387 (0.9); 4.2301 (0.9); 4.2208 (3.8); 4.2125 (0.5); 4.2028 (5.9); 4.1936 (0.5); 4.1850 (3.9); 4.1756 (1.0); 4.1671 (1.0); 4.1578 (0.9); 3.7381 (0.5); 3.3282 (10.0); 2.8914 (0.7); 2.7324 (0.6); 2.5248 (0.4); 2.5200 (0.6); 2.5112 (8.6); 2.5069 (17.2); 2.5024 (22.4); 2.4978 (16.5); 2.4934 (8.2); 2.4021 (15.0); 2.3872 (0.4); 1.2388 (8.0); 1.2211 (16.0); 1.2033 (7.6); −0.0002 (5.5) I.088: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.3527 (1.2); 4.1928 (0.7); 4.1751 (1.9); 4.1574 (1.9); 4.1396 (0.6); 4.0167 (0.9); 3.9939 (0.7); 3.3259 (7.0); 2.5202 (0.4); 2.5115 (4.5); 2.5071 (9.2); 2.5026 (12.2); 2.4980 (9.1); 2.4935 (4.5); 2.3940 (7.4); 1.3948 (16.0); 1.2013 (2.0); 1.1836 (4.2); 1.1659 (1.9); −0.0002 (3.0) I.089: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.8695 (2.6); 8.8526 (2.6); 4.1929 (0.4); 4.1751 (1.0); 4.1660 (1.0); 4.1573 (1.2); 4.1482 (3.0); 4.1423 (1.4); 4.1304 (3.2); 4.1247 (3.1); 4.1124 (1.4); 4.1069 (2.9); 4.0977 (1.1); 4.0893 (1.0); 4.0799 (0.9); 3.6603 (2.1); 3.6432 (2.3); 3.6369 (2.3); 3.6198 (2.0); 3.3332 (155.9); 2.5063 (20.8); 2.5024 (25.8); 2.4161 (26.9); 1.2370 (0.8); 1.2173 (8.2); 1.1996 (16.0); 1.1819 (8.4); 1.1613 (0.6); 1.1485 (0.3); 0.6357 (0.4); 0.6218 (0.6); 0.6137 (1.3); 0.6006 (1.3); 0.5910 (1.5); 0.5799 (0.9); 0.5695 (0.8); 0.5525 (0.7); 0.5392 (1.1); 0.5299 (1.4); 0.5190 (1.4); 0.5090 (1.5); 0.4967 (0.7); 0.4878 (1.2); 0.4741 (1.2); 0.4641 (1.6); 0.4520 (1.9); 0.4407 (1.4); 0.4283 (0.6); 0.3904 (0.8); 0.3783 (1.4); 0.3677 (1.7); 0.3556 (1.5); 0.3452 (0.9); 0.3334 (0.4); −0.0002 (14.8) I.090: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.3480 (1.3); 4.1901 (0.7); 4.1724 (1.9); 4.1547 (1.9); 4.1369 (0.6); 4.0105 (0.9); 3.9877 (0.7); 3.3279 (9.4); 2.5120 (4.0); 2.5075 (8.2); 2.5030 (10.9); 2.4984 (8.0); 2.4939 (4.0); 2.4308 (7.5); 1.3944 (16.0); 1.1994 (2.1); 1.1817 (4.4); 1.1639 (2.0); −0.0002 (1.8) I.091: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.1898 (0.7); 9.1713 (0.7); 5.2980 (1.5); 5.2795 (1.5); 3.7365 (16.0); 3.3273 (3.4); 2.5118 (3.6); 2.5073 (7.1); 2.5027 (9.3); 2.4982 (6.8); 2.4937 (3.4); 2.4401 (8.7); −0.0002 (2.7) I.092: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6470 (1.3); 8.6286 (1.3); 4.4084 (0.5); 4.3950 (0.7); 4.3898 (0.7); 4.3864 (0.8); 4.3764 (0.8); 4.3729 (0.7); 4.3677 (0.7); 4.3541 (0.5); 4.1394 (0.7); 4.1348 (0.8); 4.1216 (2.2); 4.1171 (2.3); 4.1037 (2.3); 4.0994 (2.3); 4.0895 (0.4); 4.0859 (0.8); 4.0818 (0.7); 3.3266 (11.2); 2.8922 (0.4); 2.7328 (0.3); 2.5253 (0.4); 2.5203 (0.7); 2.5118 (8.1); 2.5075 (16.2); 2.5031 (21.3); 2.4986 (15.9); 2.4944 (8.2); 2.4231 (16.0); 1.7742 (0.4); 1.7572 (0.4); 1.7518 (0.4); 1.7391 (0.7); 1.7222 (0.7); 1.7170 (0.7); 1.6998 (0.6); 1.6493 (0.6); 1.6355 (0.8); 1.6316 (0.8); 1.6173 (0.8); 1.6007 (0.4); 1.5965 (0.5); 1.5828 (0.4); 1.2119 (4.6); 1.1941 (9.4); 1.1764 (4.5); 0.8206 (0.5); 0.8145 (0.4); 0.8024 (0.7); 0.7905 (0.5); 0.7836 (0.5); 0.4571 (0.6); 0.4476 (0.8); 0.4447 (0.8); 0.4367 (1.3); 0.4275 (1.2); 0.4167 (1.5); 0.4063 (0.8); 0.3966 (0.6); 0.1912 (0.6); 0.1818 (0.6); 0.1784 (0.7); 0.1678 (0.8); 0.1605 (0.6); 0.1500 (0.4); 0.0799 (0.4); 0.0695 (0.7); 0.0609 (0.8); 0.0506 (0.7); 0.0484 (0.7); 0.0383 (0.6); −0.0002 (4.9) I.093: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.2914 (2.2); 3.5837 (16.0); 3.3253 (10.5); 2.5247 (0.4); 2.5200 (0.6); 2.5112 (7.3); 2.5068 (14.6); 2.5022 (19.2); 2.4976 (14.1); 2.4931 (6.9); 2.3704 (15.6); 1.3201 (0.4); 1.3063 (1.0); 1.2989 (1.1); 1.2928 (0.7); 1.2853 (2.1); 1.2777 (0.7); 1.2714 (1.1); 1.2641 (1.1); 1.2503 (0.6); 0.5351 (0.4); 0.5307 (0.6); 0.5261 (0.7); 0.5218 (0.9); 0.5170 (0.7); 0.5078 (1.2); 0.5024 (1.1); 0.4967 (0.8); 0.4936 (0.8); 0.4887 (0.9); 0.4865 (0.9); 0.4648 (0.6); 0.4439 (2.3); 0.4399 (2.5); 0.4360 (2.6); 0.4327 (2.1); 0.4224 (2.1); 0.4187 (2.4); 0.4146 (2.8); 0.4114 (2.2); 0.3902 (0.5); 0.3792 (0.4); 0.3677 (0.9); 0.3636 (0.8); 0.3606 (0.8); 0.3568 (1.0); 0.3542 (1.0); 0.3491 (1.2); 0.3402 (0.7); 0.3353 (0.9); 0.3304 (0.7); 0.3265 (0.6); 0.3215 (0.4); −0.0002 (5.8) I.094: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.1574 (1.2); 9.1390 (1.2); 5.2240 (2.5); 5.2056 (2.5); 4.2459 (0.9); 4.2367 (1.0); 4.2281 (1.0); 4.2188 (3.9); 4.2103 (0.5); 4.2008 (6.0); 4.1913 (0.5); 4.1829 (4.0); 4.1735 (1.0); 4.1651 (1.0); 4.1558 (0.9); 3.3262 (7.4); 2.8919 (0.5); 2.7328 (0.5); 2.5252 (0.4); 2.5203 (0.6); 2.5117 (6.5); 2.5073 (12.8); 2.5028 (16.6); 2.4982 (12.3); 2.4939 (6.1); 2.4392 (14.2); 1.2381 (8.1); 1.2203 (16.0); 1.2025 (7.7); −0.0002 (4.2) I.095: ¹H-NMR(499.9 MHz, d₆-DMSO): δ = 8.1552 (3.7); 3.7581 (4.1); 2.5017 (7.2); 2.4034 (40.0); 2.2718 (0.5); 1.2291 (0.5); 1.1744 (3.8); 0.4475 (3.8); 0.4333 (2.9); 0.3601 (16.0); 0.0769 (0.3); 0.0643 (0.4) I.096: ¹H-NMR(499.9 MHz, d₆-DMSO): δ = 3.0745 (16.0); 2.2618 (2.2); 2.2583 (3.0); 2.2549 (2.4) I.097: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2988 (6.5); 4.4815 (8.6); 4.3068 (1.0); 4.2829 (3.2); 4.2591 (3.3); 4.2353 (1.1); 3.7849 (16.0); 2.6428 (15.9); 1.5908 (5.6); 1.3443 (3.8); 1.3205 (7.8); 1.2967 (3.7); 0.0373 (8.5) I.098: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.2988 (5.4); 4.4783 (8.4); 4.3065 (1.0); 4.2827 (3.2); 4.2588 (3.2); 4.2351 (1.1); 3.7898 (16.0); 2.5959 (0.4); 2.5930 (0.6); 2.5855 (15.9); 2.5778 (0.5); 1.5942 (3.4); 1.3440 (3.9); 1.3202 (7.8); 1.2964 (3.8); 0.0370 (7.2) I.099: ¹H-NMR(300.2 MHz, CDCl3): δ = 8.0100 (0.5); 7.2989 (6.3); 4.5637 (4.8); 4.5492 (4.7); 4.3922 (1.3); 4.3684 (4.0); 4.3445 (4.1); 4.3208 (1.4); 2.9946 (0.4); 2.5594 (16.0); 1.6056 (0.4); 1.4071 (4.9); 1.3833 (9.9); 1.3595 (4.8); 1.2933 (0.4); 0.0376 (8.5) I.100: ¹H-NMR(300.2 MHz, CDCl3): δ = 8.0546 (0.4); 7.7304 (0.9); 7.2990 (6.6); 4.2596 (1.4); 4.2358 (4.6); 4.2120 (4.8); 4.1884 (1.7); 2.9977 (4.1); 2.9176 (5.1); 2.5702 (0.9); 2.5331 (16.0); 1.8298 (1.1); 1.8122 (3.1); 1.8018 (3.2); 1.7854 (1.4); 1.6884 (0.5); 1.6774 (0.6); 1.6538 (0.9); 1.4254 (1.4); 1.4089 (3.2); 1.3987 (3.3); 1.3811 (1.2); 1.3067 (5.0); 1.2969 (0.8); 1.2830 (9.7); 1.2736 (0.9); 1.2592 (4.7); 1.2499 (0.5); 0.0362 (8.8); 0.0253 (0.3) I.101: ¹H-NMR(300.2 MHz, CDCl3): δ = 7.8352 (0.7); 7.2991 (0.7); 5.3309 (4.5); 3.7478 (16.0); 2.5126 (12.5); 2.1883 (1.0); 1.8198 (1.0); 1.8021 (2.5); 1.7918 (2.5); 1.7752 (1.2); 1.4297 (1.2); 1.4133 (2.5); 1.4030 (2.6); 1.3852 (1.0); 1.2840 (0.3); 0.0295 (0.8) I.102: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 12.6826 (1.6); 10.5243 (6.1); 3.6317 (1.4); 3.3498 (16.0); 2.5344 (4.2); 2.5284 (8.8); 2.5223 (12.1); 2.5163 (8.6); 2.5103 (4.0); 2.4325 (1.4); 2.3505 (44.1); 2.0951 (5.4); 1.5652 (2.5); 1.5480 (6.3); 1.5373 (7.1); 1.5227 (3.1); 1.4711 (0.3); 1.4623 (0.3); 1.3087 (3.2); 1.2940 (6.7); 1.2834 (6.4); 1.2663 (2.3); 0.0313 (0.5); 0.0204 (14.2); 0.0095 (0.4) I.103: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 12.2508 (0.4); 8.6871 (1.2); 8.6623 (1.2); 7.9729 (0.5); 4.4687 (0.4); 4.4512 (0.5); 4.4437 (0.5); 4.4371 (0.6); 4.4265 (0.6); 4.4198 (0.6); 4.4124 (0.6); 4.3949 (0.4); 3.6811 (16.0); 3.3514 (1.9); 2.9111 (4.1); 2.7521 (3.5); 2.7506 (3.1); 2.5345 (1.2); 2.5285 (2.6); 2.5224 (3.6); 2.5164 (2.6); 2.5105 (1.2); 2.4044 (17.3); 2.3701 (2.7); 2.3457 (1.5); 2.1297 (0.3); 2.1091 (0.5); 2.0952 (0.6); 2.0835 (0.7); 2.0656 (0.5); 1.9835 (0.5); 1.9755 (0.4); 1.9596 (0.5); 1.9521 (0.6); 1.9371 (0.4); 1.9282 (0.4); 0.0193 (2.4) I.104: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 12.2412 (0.5); 8.6790 (1.3); 8.6543 (1.3); 4.4624 (0.4); 4.4448 (0.5); 4.4373 (0.6); 4.4308 (0.7); 4.4203 (0.6); 4.4136 (0.6); 4.4062 (0.6); 4.3887 (0.4); 3.6794 (16.0); 3.3487 (2.6); 2.5346 (1.4); 2.5286 (2.9); 2.5226 (4.0); 2.5165 (2.9); 2.5106 (1.4); 2.4409 (16.6); 2.3916 (1.1); 2.3673 (2.7); 2.3429 (1.5); 2.1234 (0.3); 2.1032 (0.5); 2.0770 (0.7); 2.0591 (0.5); 1.9769 (0.5); 1.9530 (0.5); 1.9455 (0.6); 1.9306 (0.4); 1.9216 (0.4); 0.0198 (1.4) I.105: ¹H-NMR(600.4 MHz, d₆-DMSO): δ = 12.3575 (0.5); 8.3943 (0.7); 8.3799 (0.9); 8.3640 (0.5); 7.2470 (0.8); 7.2445 (0.5); 7.2351 (2.2); 7.2329 (1.8); 7.2274 (0.7); 7.2233 (3.2); 7.2083 (4.6); 7.2049 (2.3); 7.1966 (2.2); 7.1918 (1.6); 7.1867 (0.3); 7.1803 (0.4); 5.7520 (0.4); 4.7305 (0.6); 4.7220 (0.6); 4.7169 (0.4); 4.7082 (0.3); 4.4758 (0.5); 4.4664 (0.6); 4.4622 (0.8); 4.4533 (0.7); 4.4492 (0.6); 4.4396 (0.5); 3.5919 (16.0); 3.3039 (46.0); 3.0388 (0.6); 3.0296 (0.6); 3.0157 (1.1); 3.0065 (1.0); 2.9713 (1.1); 2.9567 (1.1); 2.9482 (0.6); 2.9337 (0.6); 2.7294 (0.4); 2.7210 (0.5); 2.7011 (0.7); 2.6931 (0.7); 2.6150 (1.7); 2.6119 (1.6); 2.6088 (1.1); 2.6057 (0.6); 2.6011 (0.8); 2.5882 (0.5); 2.5733 (0.5); 2.5209 (2.7); 2.5179 (3.2); 2.5147 (3.1); 2.5060 (73.9); 2.5029 (158.0); 2.4999 (219.6); 2.4968 (160.8); 2.4938 (75.9); 2.3898 (0.4); 2.3868 (1.0); 2.3838 (1.4); 2.3807 (1.0); 2.3778 (0.6); 2.3670 (12.3); 0.0053 (1.4); −0.0001 (48.2); −0.0057 (1.5) I.106: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6802 (2.6); 7.9525 (0.9); 4.0926 (1.3); 4.0749 (4.2); 4.0572 (4.3); 4.0394 (1.4); 3.3508 (31.4); 3.3446 (41.5); 2.8944 (5.8); 2.7352 (5.2); 2.5271 (0.4); 2.5096 (13.6); 2.5052 (17.7); 2.5008 (13.1); 2.3767 (16.0); 2.1321 (0.3); 2.1120 (0.9); 2.0993 (0.8); 2.0910 (0.9); 2.0783 (1.6); 2.0589 (0.7); 2.0264 (0.7); 2.0120 (1.8); 1.9961 (1.1); 1.9789 (1.0); 1.9633 (0.5); 1.7234 (0.4); 1.7077 (2.1); 1.6987 (2.5); 1.6913 (4.4); 1.6813 (2.5); 1.6727 (1.9); 1.1647 (4.4); 1.1470 (9.0); 1.1293 (4.3); −0.0002 (0.4) I.107: ¹H-NMR(600.4 MHz, d₆-DMSO): δ = 8.6920 (2.0); 3.7399 (0.6); 3.7335 (1.2); 3.7269 (0.7); 3.7203 (0.9); 3.7137 (1.6); 3.7074 (0.8); 3.6307 (16.0); 3.5939 (0.8); 3.5864 (0.7); 3.5791 (0.9); 3.5722 (1.1); 3.5667 (0.6); 3.5596 (0.7); 3.5519 (0.6); 3.3034 (39.2); 2.6149 (0.6); 2.6119 (0.8); 2.6088 (0.6); 2.5209 (1.7); 2.5179 (2.0); 2.5148 (2.0); 2.5059 (43.4); 2.5029 (91.6); 2.4999 (126.5); 2.4968 (92.7); 2.4939 (44.1); 2.4318 (15.5); 2.3869 (0.6); 2.3839 (0.8); 2.3808 (0.6); 1.9814 (2.4); 1.9747 (3.5); 1.9674 (2.0); 1.9595 (1.2); 0.0053 (0.8); −0.0001 (26.8); −0.0057 (0.9) I.108: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.7880 (1.6); 8.7690 (1.7); 6.3324 (0.6); 6.2032 (0.6); 6.1923 (1.2); 6.1816 (0.6); 6.0522 (0.6); 6.0412 (0.3); 4.6377 (0.5); 4.6181 (1.2); 4.6033 (1.2); 4.5836 (0.6); 3.6887 (16.0); 3.3287 (109.3); 2.5102 (8.6); 2.4579 (0.9); 2.4371 (16.3); 2.4191 (2.0); 2.4079 (1.4); 2.3978 (1.0); 2.3766 (0.8); 2.3608 (0.6); 2.3492 (0.4) I.109: ¹H-NMR(500.1 MHz, CDCl3): δ = 7.2718 (0.9); 6.7828 (0.5); 6.7668 (0.5); 4.4990 (0.5); 4.4952 (0.4); 4.4914 (0.4); 4.4894 (0.4); 4.4855 (0.6); 4.4821 (0.6); 4.4779 (0.4); 4.4758 (0.4); 4.4721 (0.4); 4.4686 (0.5); 3.7216 (15.8); 2.6902 (0.7); 2.6799 (0.7); 2.6580 (1.5); 2.6478 (1.5); 2.6053 (1.9); 2.5962 (1.9); 2.5786 (0.4); 2.5732 (0.9); 2.5640 (0.9); 2.5270 (16.0); 1.3253 (7.0); 1.3117 (6.9); 1.2546 (0.4); 0.8812 (0.4); −0.0002 (1.1) I.110: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 8.4040 (0.9); 8.3847 (1.7); 8.3654 (0.9); 7.9082 (1.1); 7.8936 (1.1); 3.8234 (5.5); 3.8039 (5.5); 3.3510 (16.0); 2.6293 (11.0); 2.6140 (10.9); 2.5347 (2.0); 2.5287 (4.1); 2.5226 (5.6); 2.5166 (4.0); 2.5106 (2.0); 2.4358 (29.2); 0.0199 (5.8) I.111: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.5583 (1.0); 8.5378 (1.0); 4.8124 (0.4); 4.7936 (0.7); 4.7803 (0.6); 4.7742 (0.6); 4.7608 (0.7); 4.7422 (0.5); 3.4813 (0.4); 3.4679 (0.5); 3.4533 (0.8); 3.4398 (0.9); 3.4237 (0.8); 3.4103 (0.7); 3.3479 (0.9); 3.3328 (1.0); 3.3302 (1.0); 3.3202 (0.8); 3.3098 (9.7); 2.5048 (5.9); 2.5005 (8.3); 2.4961 (6.4); 2.4690 (0.9); 2.4547 (0.6); 2.3871 (16.0); 2.3203 (0.4); 2.3026 (0.4); 2.2896 (0.8); 2.2718 (0.8); 2.2585 (0.7); 2.2406 (0.7); 0.0078 (0.4); −0.0002 (11.2); −0.0083 (0.7) I.112: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2594 (13.0); 6.8715 (1.9); 4.3348 (1.4); 4.3174 (4.0); 4.2996 (4.0); 4.2819 (1.4); 4.2415 (0.5); 4.2238 (0.5); 3.5420 (0.7); 3.5343 (0.8); 3.5242 (2.0); 3.5170 (2.0); 3.5064 (2.0); 3.4996 (2.0); 3.4895 (0.8); 3.4818 (0.7); 2.7997 (0.4); 2.7826 (1.1); 2.7653 (1.5); 2.7481 (1.1); 2.7305 (0.5); 2.5698 (2.2); 2.5561 (16.0); 2.2421 (1.7); 1.9073 (1.7); 1.5474 (3.1); 1.3570 (4.1); 1.3394 (8.0); 1.3217 (4.1); 1.3101 (0.8); 1.2919 (1.1); 1.2749 (0.6); 1.2486 (0.4); 1.2311 (4.2); 1.2137 (8.0); 1.1963 (3.9); 1.1008 (7.6); 1.0838 (7.4); 0.9376 (7.6); 0.9203 (7.4); −0.0002 (13.8); −0.0011 (13.8) I.113: ¹H-NMR(500.1 MHz, CDCl3): δ = 7.2597 (11.4); 4.5445 (3.2); 4.5357 (3.2); 3.8645 (11.8); 2.5219 (10.6); 1.5372 (16.0); 0.0063 (0.5); −0.0002 (13.5); −0.0067 (0.5) I.114: ¹H-NMR(500.1 MHz, CDCl3): δ = 7.4047 (1.4); 7.2625 (1.7); 4.4791 (1.3); 4.4595 (1.3); 3.8166 (16.0); 2.4892 (15.1); 1.4919 (0.3); 1.4856 (0.6); 1.4794 (0.3); 1.4759 (0.4); 1.4722 (0.4); 1.4661 (0.6); 1.4597 (0.4); 0.8166 (0.3); 0.8085 (0.7); 0.8042 (0.5); 0.8013 (0.6); 0.7962 (0.4); 0.7924 (0.5); 0.7878 (0.5); 0.7835 (0.4); 0.7802 (0.6); 0.6590 (0.5); 0.6511 (1.4); 0.6425 (1.5); 0.6389 (1.3); 0.6362 (1.2); 0.6314 (0.8); 0.6284 (1.0); 0.6239 (0.4); 0.6197 (0.5); 0.5153 (0.4); 0.5094 (0.3); 0.5055 (0.8); 0.5028 (0.8); 0.4962 (0.4); 0.4934 (0.6); 0.4839 (0.4); −0.0002 (1.7) I.115: ¹H-NMR(499.9 MHz, d₆-DMSO): δ = 10.7436 (0.4); 8.9433 (1.4); 8.2829 (1.5); 8.2657 (1.5); 4.0357 (1.1); 4.0184 (2.1); 4.0011 (1.1); 3.3241 (3.0); 2.5068 (2.7); 2.5033 (3.4); 2.5000 (2.4); 2.4245 (0.9); 2.4151 (0.6); 2.3978 (16.0); 2.1847 (0.3); 2.0493 (0.6); 2.0358 (0.8); 2.0219 (0.8); 2.0190 (0.8); 2.0054 (0.6); 0.9505 (0.4); 0.9363 (0.4); 0.9151 (6.8); 0.9017 (7.1); 0.8928 (6.8); 0.8793 (6.2); 0.8159 (0.4) I.116: ¹H-NMR(300.2 MHz, d₆-DMSO): δ = 11.0150 (7.1); 4.4515 (14.8); 4.2003 (2.1); 4.1766 (6.7); 4.1529 (6.8); 4.1293 (2.2); 3.3510 (6.2); 2.5338 (2.8); 2.5281 (5.8); 2.5221 (7.8); 2.5161 (5.8); 2.5100 (3.2); 2.4961 (31.4); 2.4753 (0.8); 1.2487 (7.5); 1.2250 (16.0); 1.2013 (7.2); 0.0190 (5.5) I.117: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2645 (2.1); 6.6188 (0.8); 6.6009 (0.8); 4.7953 (0.6); 4.7829 (0.8); 4.7767 (1.2); 4.7646 (1.2); 4.7583 (0.7); 4.7460 (0.6); 3.7998 (15.9); 3.0241 (0.4); 3.0080 (0.5); 3.0032 (0.5); 2.9886 (1.0); 2.9732 (0.9); 2.9684 (0.9); 2.9525 (0.8); 2.9031 (0.7); 2.8865 (1.0); 2.8827 (0.9); 2.8668 (1.0); 2.8517 (0.6); 2.8478 (0.5); 2.8313 (0.4); 2.5339 (15.8); 2.3369 (16.0); 2.2815 (0.4); 2.2779 (0.4); 2.2732 (0.3); 2.2653 (0.4); 2.2587 (0.7); 2.2451 (0.7); 2.2377 (0.5); 2.2299 (0.5); 2.2252 (0.5); 2.2093 (0.3); 2.1161 (0.4); 2.0974 (0.7); 2.0804 (1.0); 2.0611 (0.8); 2.0447 (0.5); 1.6090 (3.1); −0.0002 (2.2) I.118: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7480 (1.1); 8.7287 (1.1); 4.8056 (0.5); 4.7906 (0.7); 4.7859 (1.1); 4.7713 (1.1); 4.7665 (0.7); 4.7516 (0.5); 3.6617 (15.5); 3.6231 (16.0); 3.3300 (8.8); 2.9747 (0.8); 2.9601 (0.8); 2.9338 (1.6); 2.9192 (1.4); 2.8559 (1.5); 2.8359 (1.5); 2.8150 (0.8); 2.7950 (0.8); 2.5256 (0.4); 2.5073 (9.8); 2.5029 (12.7); 2.4984 (9.3); 2.4942 (4.6); 2.3664 (16.0); −0.0002 (1.2) I.119: ¹H-NMR(600.1 MHz, d₆-DMSO): δ = 8.7134 (1.3); 8.7007 (1.3); 4.5415 (0.6); 4.5339 (0.6); 4.5287 (0.6); 4.5256 (0.8); 4.5212 (0.7); 4.5180 (0.7); 4.5128 (0.7); 4.5051 (0.6); 3.6794 (16.0); 3.4712 (1.0); 3.4636 (1.1); 3.4480 (1.3); 3.4403 (1.2); 3.3740 (5.8); 3.3693 (5.9); 3.3634 (5.6); 3.3596 (5.8); 3.3539 (6.8); 3.3526 (6.8); 3.3499 (6.1); 3.3458 (6.4); 3.3436 (7.0); 3.3401 (8.5); 3.3382 (9.4); 3.3361 (12.0); 3.2015 (1.2); 3.1855 (1.2); 3.1783 (1.0); 3.1623 (1.0); 2.9287 (15.6); 2.8919 (1.0); 2.7333 (0.6); 2.7324 (0.8); 2.5101 (4.6); 2.5070 (10.3); 2.5039 (14.6); 2.5008 (10.4); 2.4978 (4.6); 2.3924 (14.4) I.120: ¹H-NMR(600.1 MHz, d₆-DMSO): δ = 8.6723 (1.4); 8.6596 (1.4); 8.2839 (0.6); 8.2752 (1.1); 8.2664 (0.6); 4.5215 (0.4); 4.5138 (0.5); 4.5086 (0.6); 4.5058 (0.7); 4.5012 (0.6); 4.4983 (0.6); 4.4931 (0.5); 4.4854 (0.4); 3.6744 (15.9); 3.4419 (0.9); 3.4342 (0.9); 3.4185 (1.1); 3.4109 (1.2); 3.3828 (7.7); 3.3803 (8.1); 3.3749 (8.5); 3.3731 (8.4); 3.3711 (9.0); 3.3681 (9.1); 3.3645 (12.6); 3.3630 (12.5); 3.3604 (11.5); 3.3594 (11.3); 3.3568 (16.6); 3.3529 (20.6); 3.3506 (25.3); 3.1521 (1.2); 3.1412 (1.0); 3.1358 (1.4); 3.1320 (1.6); 3.1290 (1.8); 3.1202 (1.4); 3.1118 (1.4); 3.0991 (0.4); 2.8923 (0.4); 2.5110 (4.8); 2.5079 (10.8); 2.5049 (15.2); 2.5018 (10.9); 2.4987 (4.9); 2.3924 (16.0); 1.0285 (2.9); 1.0165 (5.8); 1.0045 (2.8) I.121: ¹H-NMR(600.1 MHz, d₆-DMSO): δ = 10.0824 (0.4); 10.0762 (1.0); 10.0689 (1.0); 8.7850 (1.6); 8.7720 (1.6); 7.9525 (0.8); 5.8156 (0.3); 4.6751 (0.7); 4.6674 (0.8); 4.6621 (0.7); 4.6584 (0.9); 4.6544 (0.9); 4.6507 (0.8); 4.6454 (0.8); 4.6376 (0.7); 3.9564 (1.1); 3.9487 (1.2); 3.9331 (1.3); 3.9254 (1.2); 3.7596 (0.9); 3.7056 (0.4); 3.7008 (1.5); 3.6923 (16.0); 3.6795 (1.8); 3.6755 (0.5); 3.6704 (0.4); 3.5091 (1.2); 3.4923 (1.3); 3.4858 (1.2); 3.4690 (1.2); 3.4156 (17.6); 3.4134 (17.5); 3.4082 (19.5); 3.3954 (28.7); 3.3925 (28.4); 3.3888 (40.3); 3.3825 (56.3); 3.3631 (0.7); 3.0293 (7.8); 3.0219 (7.9); 2.9194 (0.7); 2.9110 (0.8); 2.8941 (8.2); 2.7345 (6.8); 2.5258 (0.4); 2.5140 (6.3); 2.5110 (14.2); 2.5079 (20.0); 2.5048 (14.2); 2.5018 (6.3); 2.4378 (0.8); 2.3980 (1.5); 2.3906 (14.6); 2.3797 (0.5); 2.3681 (1.8) I.122: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.6648 (1.1); 8.6461 (1.1); 4.4378 (0.4); 4.4246 (0.6); 4.4190 (0.6); 4.4141 (0.7); 4.4059 (0.6); 4.4009 (0.6); 4.3954 (0.6); 4.3822 (0.5); 3.6610 (15.3); 3.5943 (16.0); 3.3299 (7.4); 2.5120 (5.2); 2.5076 (10.0); 2.5031 (12.9); 2.4986 (9.3); 2.4941 (4.5); 2.4628 (1.0); 2.4598 (1.0); 2.4435 (2.6); 2.4239 (1.6); 2.3823 (15.9); 2.1384 (0.4); 2.1247 (0.6); 2.1093 (0.4); 2.1036 (0.7); 2.0903 (0.6); 2.0006 (0.5); 1.9980 (0.4); 1.9936 (0.4); 1.9817 (0.5); 1.9769 (0.5); 1.9654 (0.4); 1.9580 (0.5); 1.9418 (0.3); −0.0002 (1.8) I.123: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7380 (1.2); 8.7185 (1.2); 4.7783 (0.5); 4.7632 (0.7); 4.7587 (1.2); 4.7438 (1.1); 4.7392 (0.7); 4.7242 (0.5); 4.1464 (1.2); 4.1287 (3.9); 4.1110 (4.6); 4.0966 (2.6); 4.0935 (3.5); 4.0788 (2.4); 4.0760 (2.3); 4.0610 (0.8); 4.0585 (0.8); 3.3289 (9.5); 2.9426 (0.7); 2.9277 (0.8); 2.9019 (1.5); 2.8871 (1.4); 2.8295 (1.4); 2.8097 (1.4); 2.7888 (0.8); 2.7690 (0.8); 2.5255 (0.4); 2.5117 (5.5); 2.5074 (10.8); 2.5029 (14.0); 2.4984 (10.1); 2.4940 (4.9); 2.3672 (16.0); 1.1980 (8.0); 1.1803 (16.0); 1.1625 (7.7); −0.0002 (1.8) I.124: ¹H-NMR(600.1 MHz, d₆-DMSO): δ = 8.6436 (1.3); 8.6312 (1.3); 4.4012 (0.5); 4.3925 (0.6); 4.3889 (0.7); 4.3855 (0.8); 4.3801 (0.7); 4.3767 (0.8); 4.3730 (0.8); 4.3641 (0.5); 4.1469 (0.3); 4.1407 (0.6); 4.1348 (1.0); 4.1289 (2.0); 4.1230 (2.2); 4.1170 (2.2); 4.1111 (2.0); 4.1051 (1.0); 4.0993 (0.6); 4.0932 (0.4); 4.0752 (1.4); 4.0634 (4.3); 4.0515 (4.4); 4.0397 (1.4); 3.3808 (6.7); 3.3756 (6.8); 3.3719 (6.7); 3.3673 (6.2); 3.3635 (5.9); 3.3607 (5.7); 3.3567 (5.8); 3.3544 (5.7); 3.3504 (6.2); 3.3470 (6.7); 3.3407 (6.4); 3.3354 (6.4); 3.3320 (6.6); 3.3296 (7.3); 3.3269 (9.0); 2.5209 (0.3); 2.5091 (6.2); 2.5060 (13.9); 2.5029 (19.6); 2.4999 (13.8); 2.4968 (6.1); 2.4402 (0.9); 2.4328 (1.0); 2.4272 (1.9); 2.4226 (1.6); 2.4196 (1.6); 2.4145 (1.1); 2.4090 (1.2); 2.3899 (0.4); 2.3821 (16.0); 2.3802 (9.1); 2.1234 (0.3); 2.1190 (0.6); 2.1096 (0.9); 2.0999 (0.5); 2.0958 (0.9); 2.0869 (0.7); 2.0831 (0.4); 2.0742 (0.3); 1.9939 (0.3); 1.9835 (0.4); 1.9806 (0.5); 1.9783 (0.5); 1.9702 (0.6); 1.9677 (0.7); 1.9648 (0.5); 1.9602 (0.4); 1.9576 (0.4); 1.9543 (0.6); 1.9443 (0.4); 1.9418 (0.4); 1.2077 (4.7); 1.1959 (9.9); 1.1944 (5.6); 1.1860 (5.3); 1.1841 (7.3); 1.1742 (9.8); 1.1724 (5.4); 1.1623 (4.7); 1.1606 (2.6); −0.0001 (1.4); −0.0025 (0.5) I.125: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7136 (0.5); 8.6938 (0.5); 4.7745 (0.5); 4.7601 (0.4); 3.6607 (6.2); 3.3295 (4.5); 2.8644 (0.4); 2.8499 (0.4); 2.8241 (0.6); 2.8097 (0.6); 2.7245 (0.6); 2.7038 (0.6); 2.6842 (0.4); 2.6636 (0.4); 2.5114 (2.6); 2.5074 (5.0); 2.5029 (6.4); 2.4985 (4.7); 2.4943 (2.3); 2.3691 (6.6); 1.3930 (16.0); −0.0002 (0.7) I.126: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.5091 (1.2); 8.4894 (1.2); 4.5278 (0.6); 4.5146 (0.7); 4.5077 (1.2); 4.4947 (1.2); 4.4877 (0.7); 4.4745 (0.6); 4.1412 (0.9); 4.1392 (0.9); 4.1235 (2.8); 4.1215 (2.8); 4.1056 (2.9); 4.1039 (2.8); 4.0877 (1.0); 3.5709 (1.1); 3.5577 (1.1); 3.5366 (1.4); 3.5234 (1.3); 3.3299 (10.3); 3.3146 (1.5); 3.3008 (1.1); 3.2803 (1.1); 2.5262 (0.4); 2.5128 (6.4); 2.5085 (12.6); 2.5040 (16.2); 2.4995 (11.9); 2.4950 (6.4); 2.4880 (17.8); 1.8535 (16.0); 1.2080 (4.8); 1.1903 (10.0); 1.1725 (4.6); −0.0002 (1.5) I.127: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.6297 (1.6); 7.2607 (7.9); 5.0378 (0.3); 5.0194 (1.2); 5.0011 (1.8); 4.9825 (1.2); 4.9644 (0.4); 2.5066 (16.0); 2.3678 (0.6); 2.3612 (0.8); 2.3426 (1.7); 2.3371 (1.7); 2.3301 (1.6); 2.3232 (1.7); 2.3172 (1.9); 2.2991 (0.9); 2.1058 (0.4); 2.0810 (1.5); 2.0745 (1.1); 2.0611 (1.6); 2.0558 (2.0); 2.0371 (1.2); 2.0306 (1.5); 2.0059 (0.8); 1.8229 (0.4); 1.7975 (1.1); 1.7748 (2.2); 1.7622 (4.4); 1.7547 (4.4); 1.7423 (2.0); 1.6649 (0.4); 1.6396 (0.8); 1.6191 (1.3); 1.5928 (1.3); 1.5661 (1.7); 1.5570 (1.7); 1.3709 (1.7); 1.3584 (4.1); 1.3510 (4.1); 1.3378 (1.5); 1.2629 (0.6); 0.8818 (0.5); −0.0002 (10.2) I.128: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 9.1767 (6.4); 3.3327 (9.8); 2.8280 (2.3); 2.8096 (7.2); 2.7911 (7.4); 2.7728 (2.7); 2.5092 (6.4); 2.4601 (28.8); 1.5407 (2.3); 1.5286 (6.4); 1.5201 (7.2); 1.5096 (3.2); 1.4697 (0.4); 1.2971 (2.9); 1.2865 (7.0); 1.2779 (6.7); 1.2659 (2.6); 1.1671 (7.8); 1.1487 (16.0); 1.1303 (7.8) I.129: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.6091 (14.3); 7.2993 (5.2); 7.0543 (5.4); 3.3359 (25.4); 2.5092 (13.5); 2.4202 (62.9); 2.2559 (0.5); 1.3265 (5.5); 1.3153 (14.6); 1.3076 (16.0); 1.2974 (7.1); 1.2573 (0.8); 1.2394 (0.5); 1.0136 (0.4); 0.9739 (6.3); 0.9637 (15.4); 0.9559 (15.3); 0.9448 (6.2); 0.9065 (0.6) I.130: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.5824 (13.6); 7.7936 (5.2); 7.7835 (5.3); 4.1123 (0.7); 4.0992 (0.7); 3.3357 (15.6); 3.1823 (2.8); 3.1693 (2.8); 2.5939 (30.4); 2.5827 (30.8); 2.5092 (12.7); 2.4327 (58.7); 2.2688 (0.4); 1.3639 (0.4); 1.3276 (5.6); 1.3166 (14.8); 1.3089 (16.0); 1.2989 (7.1); 1.2588 (0.8); 1.2410 (0.6); 1.0124 (0.5); 0.9723 (6.5); 0.9621 (15.4); 0.9545 (15.2); 0.9435 (6.2); 0.9046 (0.6) I.131: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 9.0333 (3.0); 3.6450 (16.0); 3.3351 (3.7); 2.5865 (0.8); 2.5652 (1.4); 2.5537 (1.5); 2.5401 (1.7); 2.5094 (3.1); 2.4228 (15.6); 2.3160 (0.9); 2.2933 (1.9); 2.2646 (1.8); 2.2424 (1.0); 1.9881 (0.4); 1.9744 (0.8); 1.9555 (1.5); 1.9359 (1.8); 1.9147 (1.0); 1.8940 (0.3) I.132: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 9.0439 (5.8); 4.1289 (2.6); 4.1113 (7.8); 4.0936 (7.8); 4.0759 (2.7); 3.3349 (7.4); 3.1823 (0.5); 3.1692 (0.5); 2.5780 (1.5); 2.5563 (2.6); 2.5450 (2.9); 2.5313 (3.2); 2.5093 (7.4); 2.4184 (29.4); 2.3411 (0.4); 2.3080 (1.6); 2.2854 (3.5); 2.2566 (3.5); 2.2345 (1.8); 1.9980 (0.4); 1.9848 (0.8); 1.9716 (1.6); 1.9524 (2.8); 1.9327 (3.4); 1.9114 (1.9); 1.8906 (0.6); 1.1855 (7.9); 1.1678 (16.0); 1.1501 (8.0) I.133: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 9.0493 (6.1); 4.0346 (5.0); 4.0186 (10.3); 4.0027 (5.3); 3.3347 (10.8); 3.1821 (0.4); 3.1690 (0.4); 2.5808 (1.5); 2.5603 (2.7); 2.5478 (2.9); 2.5347 (3.3); 2.5097 (8.0); 2.4200 (30.4); 2.3764 (0.5); 2.3160 (1.7); 2.2938 (3.6); 2.2644 (3.5); 2.2424 (1.8); 1.9739 (1.5); 1.9612 (2.9); 1.9515 (2.5); 1.9401 (3.5); 1.9195 (2.0); 1.8988 (0.6); 1.6104 (0.6); 1.5927 (2.6); 1.5756 (5.3); 1.5578 (5.5); 1.5409 (3.1); 1.5232 (0.9); 0.8822 (8.0); 0.8638 (16.0); 0.8453 (7.7) I.134: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 9.1964 (6.7); 3.3347 (11.4); 2.8083 (4.6); 2.7906 (9.0); 2.7727 (5.1); 2.5093 (9.0); 2.4586 (29.5); 1.5252 (7.7); 1.5144 (9.8); 1.4932 (6.5); 1.4750 (3.5); 1.4571 (1.1); 1.2954 (3.0); 1.2848 (7.1); 1.2762 (7.0); 1.2644 (2.8); 0.9128 (8.1); 0.8945 (16.0); 0.8762 (7.7) I.135: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.5124 (14.6); 7.9000 (5.5); 7.8800 (5.8); 4.2934 (0.5); 4.2721 (2.4); 4.2517 (4.8); 4.2310 (4.9); 4.2099 (2.7); 4.1899 (0.8); 3.3354 (60.4); 2.5092 (25.0); 2.4396 (60.1); 2.3355 (0.4); 2.2752 (0.4); 2.1921 (0.3); 2.1010 (6.3); 2.0925 (7.0); 2.0827 (7.6); 2.0418 (2.5); 2.0170 (6.2); 1.9928 (8.5); 1.9688 (5.6); 1.9423 (1.8); 1.6187 (2.9); 1.6047 (5.3); 1.5954 (6.3); 1.5787 (7.8); 1.5608 (4.7); 1.5340 (1.7); 1.5069 (0.6); 1.3622 (1.9); 1.3192 (5.4); 1.3081 (14.6); 1.3004 (16.0); 1.2903 (7.2); 1.2496 (0.9); 1.0063 (0.5); 0.9655 (6.3); 0.9552 (15.3); 0.9475 (15.2); 0.9364 (6.3); 0.8983 (0.6) I.136: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2601 (6.3); 6.6863 (1.0); 6.6698 (1.0); 4.7704 (0.6); 4.7518 (1.3); 4.7392 (1.3); 4.7206 (0.6); 3.7903 (16.0); 3.6770 (15.8); 2.7836 (0.3); 2.5565 (15.8); 2.5342 (0.4); 2.5156 (0.6); 2.4913 (0.9); 2.4729 (1.9); 2.4607 (1.2); 2.4547 (1.4); 2.4441 (2.0); 2.4270 (1.2); 2.4018 (0.5); 2.3848 (0.4); 2.3421 (0.4); 2.3244 (0.5); 2.3065 (0.8); 2.2933 (0.8); 2.2891 (0.9); 2.2759 (0.8); 2.2578 (0.3); 2.1765 (0.4); 2.1588 (1.1); 2.1405 (1.3); 2.1228 (1.0); 2.1045 (0.7); 1.5517 (4.6); −0.0002 (8.2) I.137: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 12.5221 (0.5); 12.4517 (1.6); 12.4063 (1.0); 8.8660 (16.0); 4.0544 (0.3); 4.0376 (1.0); 4.0195 (1.0); 4.0022 (0.4); 3.6371 (0.5); 3.3267 (57.3); 3.1535 (0.4); 2.6710 (0.6); 2.5797 (0.5); 2.5511 (3.2); 2.5323 (7.7); 2.5017 (82.1); 2.4575 (2.3); 2.4197 (76.9); 2.3279 (1.1); 2.3049 (4.1); 2.2830 (9.5); 2.2552 (8.8); 2.2312 (4.4); 1.9890 (4.1); 1.9684 (2.9); 1.9488 (9.1); 1.9290 (12.6); 1.9089 (8.9); 1.8894 (2.5); 1.2368 (0.7); 1.1930 (1.1); 1.1745 (2.1); 1.1564 (1.1); −0.0002 (22.7); −0.0342 (0.4) I.138: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.7417 (2.1); 8.7247 (2.3); 7.3467 (2.0); 6.8492 (2.0); 4.3821 (0.7); 4.3519 (1.4); 4.3301 (0.8); 3.6560 (16.0); 3.3095 (7.3); 2.5002 (12.0); 2.4319 (16.3); 2.2194 (1.9); 2.2015 (4.7); 2.1839 (3.0); 2.0906 (0.4); 2.0752 (0.7); 2.0587 (1.1); 2.0402 (1.3); 2.0261 (1.0); 1.9880 (0.7); 1.9459 (0.5); 1.9269 (1.0); 1.9056 (1.2); 1.8893 (1.0); 1.8702 (0.7); 1.1734 (0.4); −0.0002 (11.8) I.139: ¹H-NMR(600.4 MHz, d₆-DMSO): δ = 8.7166 (2.4); 8.2947 (2.2); 4.1135 (1.4); 4.1017 (4.5); 4.0899 (4.6); 4.0781 (1.4); 3.7482 (0.7); 3.7418 (1.5); 3.7353 (0.8); 3.7286 (1.0); 3.7221 (2.0); 3.7158 (0.9); 3.5945 (0.8); 3.5868 (0.8); 3.5801 (1.0); 3.5728 (1.2); 3.5666 (0.7); 3.5608 (0.8); 3.5525 (0.7); 3.4250 (2.8); 3.3918 (15.5); 3.3874 (19.6); 3.3855 (21.4); 3.3819 (29.0); 3.3777 (65.1); 3.3753 (100.6); 3.3522 (0.9); 2.5131 (6.0); 2.5100 (13.5); 2.5069 (19.1); 2.5038 (13.6); 2.5008 (6.1); 2.4337 (16.0); 1.9798 (2.8); 1.9729 (4.0); 1.9659 (2.6); 1.9585 (1.4); 1.1745 (4.5); 1.1627 (9.4); 1.1509 (4.5) I.140: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.9449 (1.0); 8.9279 (1.0); 7.3880 (4.7); 7.3766 (12.1); 7.3667 (0.6); 7.3637 (0.6); 7.3536 (1.1); 7.3458 (0.8); 7.3437 (0.7); 7.3414 (0.8); 7.3319 (0.8); 7.3195 (0.4); 5.2342 (1.3); 5.2025 (3.2); 5.1636 (3.2); 5.1320 (1.3); 3.7494 (1.0); 3.7322 (1.0); 3.7255 (1.1); 3.7083 (1.0); 3.3431 (19.1); 2.8954 (0.4); 2.5302 (0.4); 2.5254 (0.7); 2.5168 (7.9); 2.5123 (15.6); 2.5077 (20.1); 2.5031 (14.5); 2.4986 (6.9); 2.3592 (16.0); 1.2531 (0.5); 1.2495 (0.5); 1.2412 (0.6); 1.2330 (0.4); 1.2294 (0.5); 0.6314 (0.4); 0.6289 (0.4); 0.6255 (0.4); 0.6175 (0.5); 0.6079 (0.7); 0.5966 (0.4); 0.5876 (0.3); 0.5613 (0.4); 0.5573 (0.4); 0.5476 (0.6); 0.5414 (0.4); 0.5370 (0.6); 0.5282 (0.8); 0.5243 (0.5); 0.5159 (0.6); 0.5116 (0.7); 0.5093 (0.7); 0.5045 (0.8); 0.4918 (0.7); 0.4817 (0.5); 0.4141 (0.3); 0.4028 (0.5); 0.3916 (0.6); 0.3793 (0.6); 0.3703 (0.4) I.141: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.0530 (1.8); 7.9574 (0.4); 4.9411 (0.4); 4.9255 (1.1); 4.9099 (1.5); 4.8943 (1.1); 4.8787 (0.4); 3.3438 (23.0); 2.8959 (2.7); 2.7368 (2.2); 2.7357 (2.2); 2.5600 (0.5); 2.5554 (0.3); 2.5443 (0.7); 2.5382 (1.0); 2.5255 (1.4); 2.5166 (8.0); 2.5122 (15.1); 2.5076 (18.8); 2.5030 (13.6); 2.4984 (6.6); 2.3769 (16.0); 2.2992 (0.5); 2.2794 (0.9); 2.2762 (1.1); 2.2563 (0.8); 2.2469 (1.0); 2.2248 (0.5); 1.9665 (0.4); 1.9626 (0.5); 1.9539 (0.5); 1.9450 (0.8); 1.9393 (0.8); 1.9247 (1.1); 1.9169 (0.5); 1.9031 (0.6); 1.1739 (14.8); 1.1583 (14.6) I.142: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.0936 (2.1); 7.9580 (0.5); 3.6307 (16.0); 3.3390 (14.7); 2.8962 (3.3); 2.7369 (2.8); 2.5300 (0.5); 2.5166 (8.3); 2.5122 (15.8); 2.5076 (20.3); 2.5031 (14.8); 2.4986 (7.1); 2.4603 (2.3); 2.4264 (2.7); 2.3878 (16.0); 2.1206 (2.7); 2.0865 (2.2); 1.2069 (9.7); 1.1311 (9.9) I.143: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.3546 (1.9); 3.6922 (15.9); 3.3691 (0.4); 3.3396 (11.3); 3.3041 (0.8); 3.2993 (1.0); 3.2659 (0.5); 3.0241 (0.4); 3.0022 (0.6); 2.9891 (0.7); 2.9670 (0.8); 2.9637 (0.8); 2.9509 (0.4); 2.9286 (0.4); 2.8963 (0.5); 2.7373 (0.4); 2.7360 (0.4); 2.5303 (0.4); 2.5256 (0.6); 2.5169 (6.7); 2.5124 (13.3); 2.5078 (17.3); 2.5032 (12.5); 2.4986 (5.8); 2.3922 (16.0) I.144: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.4320 (1.9); 4.8902 (3.5); 4.8730 (4.1); 4.6794 (4.0); 4.6623 (3.4); 3.7404 (16.0); 3.3398 (21.8); 2.8963 (1.3); 2.7371 (1.1); 2.7361 (1.0); 2.5303 (0.6); 2.5256 (1.0); 2.5168 (11.8); 2.5124 (23.3); 2.5078 (30.3); 2.5032 (22.2); 2.4988 (10.8); 2.4161 (16.0) I.145: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.2889 (0.9); 3.3396 (11.6); 3.2528 (0.4); 3.2461 (0.4); 3.2145 (0.5); 2.9487 (0.4); 2.9195 (0.4); 2.8962 (0.8); 2.7371 (0.6); 2.7358 (0.6); 2.5302 (0.4); 2.5255 (0.5); 2.5168 (6.4); 2.5123 (12.9); 2.5077 (16.8); 2.5031 (12.3); 2.4986 (5.9); 2.3856 (7.5); 1.4017 (16.0) I.146: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.4538 (2.0); 4.1817 (1.3); 4.1639 (4.2); 4.1462 (4.2); 4.1285 (1.3); 3.6897 (3.6); 3.6636 (4.2); 3.4310 (4.1); 3.4049 (3.4); 3.3415 (17.6); 2.8960 (1.1); 2.7369 (0.9); 2.7358 (0.9); 2.5303 (0.4); 2.5255 (0.6); 2.5168 (7.4); 2.5123 (14.7); 2.5078 (19.1); 2.5032 (14.0); 2.4986 (6.8); 2.3957 (16.0); 1.1962 (4.3); 1.1785 (9.0); 1.1608 (4.2) I.147: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2664 (1.2); 6.5188 (1.4); 6.5083 (1.4); 4.7081 (0.7); 4.6925 (0.8); 4.6862 (1.0); 4.6798 (1.0); 4.6722 (1.0); 4.6655 (1.0); 4.6586 (0.9); 4.6435 (0.7); 4.5526 (1.0); 4.5299 (2.4); 4.5073 (1.4); 4.3781 (0.8); 4.3628 (0.9); 4.3520 (1.2); 4.3370 (1.2); 4.3282 (0.8); 4.3123 (0.6); 2.9220 (0.6); 2.9023 (0.8); 2.8888 (1.1); 2.8729 (0.9); 2.8544 (0.7); 2.4740 (16.0); 2.3531 (0.4); 2.3240 (1.0); 2.2998 (1.2); 2.2961 (1.2); 2.2718 (0.9); 1.6406 (2.6); −0.0002 (1.4) I.148: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2605 (5.8); 6.7728 (1.2); 6.7594 (1.2); 4.7830 (1.7); 4.7753 (1.7); 4.7667 (1.6); 4.3211 (1.4); 4.3036 (4.1); 4.2859 (4.1); 4.2682 (1.4); 4.0946 (0.6); 4.0630 (2.9); 4.0294 (0.6); 2.5160 (16.0); 2.2813 (0.9); 1.5621 (1.7); 1.3464 (4.3); 1.3288 (8.3); 1.3111 (4.2); −0.0002 (7.9) I.149: ¹H-NMR(500.1 MHz, CDCl3): δ = 7.9782 (0.4); 7.9688 (0.4); 7.2598 (8.5); 5.2143 (1.0); 5.2002 (1.6); 5.1860 (1.0); 3.8385 (16.0); 2.5542 (14.4); 1.6294 (7.3); 1.6152 (7.3); 1.5370 (3.2); 0.0055 (0.5); −0.0002 (11.2); −0.0065 (0.4) I.150: ¹H-NMR(500.1 MHz, CDCl3): δ = 8.0131 (0.7); 7.2606 (4.8); 5.1842 (1.2); 5.1701 (1.8); 5.1560 (1.2); 4.3105 (1.4); 4.2962 (4.2); 4.2819 (4.3); 4.2677 (1.4); 2.5539 (16.0); 1.6266 (8.2); 1.6125 (8.1); 1.5489 (3.6); 1.3472 (4.5); 1.3329 (8.8); 1.3186 (4.3); −0.0002 (5.7) I.151: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2601 (13.2); 5.6714 (1.9); 2.9554 (0.4); 2.8824 (0.4); 2.6550 (1.4); 2.6345 (1.9); 2.5576 (0.3); 2.5359 (16.0); 1.8659 (1.5); 1.8462 (1.3); 1.7424 (2.7); 1.7208 (2.7); 1.6791 (0.9); 1.6473 (0.9); 1.5373 (4.3); 1.5138 (4.4); 1.4927 (1.3); 1.4575 (0.4); 1.2696 (0.4); 1.2380 (1.1); 1.2069 (1.5); 1.1684 (2.0); 1.1391 (2.0); 1.1082 (0.9); 1.0137 (0.6); 0.9892 (1.3); 0.9612 (1.1); 0.9317 (0.4); −0.0002 (18.7) I.152: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.8000 (3.0); 7.9524 (0.4); 3.3162 (17.6); 3.2986 (0.5); 2.8904 (2.7); 2.7307 (2.4); 2.5010 (10.2); 2.4056 (19.2); 1.6194 (16.0); 1.5189 (0.4); 1.5038 (0.8); 1.4993 (0.9); 1.4926 (0.7); 1.4849 (1.4); 1.4713 (1.0); 1.4654 (0.9); 1.4518 (0.5); 0.6691 (0.3); 0.6414 (2.0); 0.6270 (4.2); 0.6112 (2.8); 0.6070 (3.2); 0.5933 (0.8); 0.5831 (0.4); 0.5200 (0.5); 0.5124 (0.7); 0.5015 (1.4); 0.4884 (1.1); 0.4765 (0.7); 0.4626 (0.3); −0.0002 (2.6) I.153: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.8800 (1.1); 8.8634 (1.1); 8.3200 (0.6); 4.9714 (1.0); 4.9529 (1.5); 4.9345 (1.0); 3.6426 (1.0); 3.6260 (1.1); 3.6193 (1.1); 3.6025 (1.0); 3.3633 (108.7); 2.5130 (30.8); 2.5086 (39.0); 2.5043 (29.6); 2.3870 (16.0); 2.3357 (0.6); 2.3292 (0.6); 2.3102 (1.1); 2.3060 (1.2); 2.2983 (1.2); 2.2862 (1.3); 2.2812 (1.1); 2.2674 (0.7); 2.2608 (0.5); 2.0516 (0.6); 2.0457 (0.5); 2.0323 (0.8); 2.0265 (0.9); 2.0212 (0.7); 2.0087 (1.0); 2.0022 (0.9); 1.9898 (0.7); 1.9845 (0.8); 1.9787 (0.7); 1.9651 (0.5); 1.9597 (0.6); 1.7771 (0.8); 1.7518 (0.8); 1.6493 (0.5); 1.6446 (0.6); 1.6241 (1.0); 1.5982 (0.8); 1.5776 (0.4); 1.2269 (0.3); 1.2160 (0.4); 1.2064 (0.7); 1.1951 (0.7); 1.1834 (0.7); 1.1721 (0.4); 1.1633 (0.3); 0.6385 (0.4); 0.6297 (0.7); 0.6222 (0.7); 0.6172 (0.7); 0.6069 (0.8); 0.5959 (0.5); 0.5859 (0.4); 0.5609 (0.4); 0.5473 (0.6); 0.5375 (0.8); 0.5267 (0.8); 0.5171 (1.0); 0.5047 (0.8); 0.4969 (0.8); 0.4913 (0.7); 0.4827 (0.9); 0.4703 (1.0); 0.4595 (0.7); 0.4468 (0.3); 0.3964 (0.4); 0.3857 (0.7); 0.3735 (0.9); 0.3612 (0.8); 0.3516 (0.5) I.154: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.8558 (1.1); 8.8389 (1.0); 4.9692 (0.4); 4.9535 (1.2); 4.9379 (1.6); 4.9223 (1.2); 4.9067 (0.4); 3.6174 (1.1); 3.6005 (1.1); 3.5939 (1.1); 3.5769 (1.1); 3.3460 (3.8); 3.3424 (6.9); 3.3374 (6.4); 3.3335 (8.6); 2.5252 (0.4); 2.5117 (7.9); 2.5075 (15.0); 2.5030 (18.8); 2.4984 (13.4); 2.4942 (6.4); 2.3805 (16.0); 1.2186 (7.5); 1.2032 (14.2); 1.1877 (7.5); 1.1721 (0.7); 1.1634 (0.4); 1.1602 (0.4); 1.1518 (0.3); 0.6118 (0.6); 0.6028 (0.6); 0.5985 (0.6); 0.5885 (0.7); 0.5831 (0.4); 0.5770 (0.4); 0.5673 (0.4); 0.5518 (0.3); 0.5419 (0.4); 0.5383 (0.5); 0.5288 (0.6); 0.5182 (0.6); 0.5083 (0.7); 0.4868 (0.6); 0.4730 (0.5); 0.4631 (0.8); 0.4508 (0.9); 0.4398 (0.7); 0.3914 (0.4); 0.3800 (0.6); 0.3684 (0.8); 0.3560 (0.7); 0.3460 (0.4); −0.0002 (0.9) I.155: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.0822 (3.0); 7.9527 (0.6); 3.9136 (5.3); 3.8958 (5.3); 3.3391 (11.8); 3.3336 (10.4); 2.8911 (3.0); 2.7314 (2.9); 2.5835 (0.8); 2.5631 (1.4); 2.5566 (1.3); 2.5463 (1.6); 2.5371 (1.7); 2.5298 (1.5); 2.5031 (25.1); 2.4994 (20.8); 2.3849 (16.0); 2.3157 (0.8); 2.2932 (1.9); 2.2637 (1.7); 2.2416 (0.9); 1.9876 (0.5); 1.9739 (0.8); 1.9609 (1.5); 1.9511 (1.3); 1.9398 (1.8); 1.9193 (0.9); 1.0852 (0.3); 1.0734 (0.7); 1.0653 (0.6); 1.0542 (1.0); 1.0432 (0.7); 1.0358 (0.7); 1.0239 (0.4); 0.4999 (0.8); 0.4884 (2.6); 0.4851 (2.9); 0.4685 (2.6); 0.4651 (2.8); 0.4547 (0.9); 0.2578 (0.9); 0.2447 (3.5); 0.2325 (3.4); 0.2207 (0.7); −0.0002 (0.7) I.156: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.9629 (0.9); 3.3431 (3.4); 3.3385 (4.4); 3.3343 (5.1); 2.5251 (0.4); 2.5119 (5.0); 2.5075 (9.4); 2.5029 (11.9); 2.4983 (8.5); 2.4938 (4.2); 2.4813 (0.5); 2.4669 (0.3); 2.3711 (7.4); 2.2517 (0.5); 2.2313 (0.4); 2.2214 (0.5); 1.9277 (0.5); 1.9154 (0.4); 1.9065 (0.6); 1.3895 (16.0); −0.0002 (0.6) I.157: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.0499 (3.4); 4.0694 (2.5); 4.0537 (5.1); 4.0378 (2.6); 3.3338 (18.4); 2.5702 (0.8); 2.5494 (1.5); 2.5367 (1.8); 2.5027 (32.3); 2.3777 (16.0); 2.3094 (0.9); 2.2871 (1.9); 2.2579 (1.8); 2.2357 (0.9); 1.9815 (0.4); 1.9679 (0.8); 1.9524 (1.5); 1.9452 (1.4); 1.9311 (1.8); 1.9102 (1.0); 1.5617 (0.5); 1.5451 (1.8); 1.5281 (2.5); 1.5088 (2.1); 1.4925 (0.8); 1.3496 (0.4); 1.3310 (1.4); 1.3121 (2.5); 1.2933 (2.5); 1.2752 (1.3); 1.2571 (0.3); 0.8707 (4.4); 0.8523 (8.3); 0.8338 (3.8); −0.0002 (0.6) I.158: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.0474 (2.0); 7.9531 (0.4); 4.7340 (0.4); 4.7248 (0.5); 4.7145 (0.7); 4.7054 (0.6); 3.3340 (12.9); 2.8913 (3.4); 2.7312 (2.8); 2.5632 (0.5); 2.5583 (0.3); 2.5427 (0.9); 2.5358 (0.8); 2.5303 (1.0); 2.5256 (1.2); 2.5119 (10.3); 2.5075 (19.9); 2.5029 (25.5); 2.4983 (18.6); 2.4938 (9.4); 2.3754 (16.0); 2.3100 (0.6); 2.2876 (1.1); 2.2670 (0.8); 2.2567 (1.1); 2.2353 (0.5); 1.9776 (0.4); 1.9639 (0.5); 1.9558 (1.1); 1.9413 (0.9); 1.9347 (1.3); 1.9273 (0.5); 1.9189 (0.5); 1.9140 (0.7); 1.7342 (0.5); 1.7246 (0.5); 1.7065 (0.9); 1.6945 (0.8); 1.6875 (0.8); 1.6231 (0.7); 1.6028 (0.7); 1.4238 (0.7); 1.4095 (0.9); 1.4021 (0.9); 1.3769 (1.2); 1.3525 (1.3); 1.3283 (0.7); 1.3211 (0.8); 1.2975 (0.7); 1.2739 (0.4); −0.0002 (0.7) I.159: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.5962 (0.9); 9.0528 (0.9); 8.6325 (2.5); 7.9527 (1.4); 3.3359 (8.2); 2.9644 (0.6); 2.8914 (9.7); 2.7320 (8.2); 2.5259 (0.5); 2.5210 (0.6); 2.5123 (6.8); 2.5078 (13.7); 2.5033 (17.6); 2.4987 (12.7); 2.4942 (6.1); 2.3660 (16.0); 1.8321 (1.1); 1.8215 (2.7); 1.8124 (2.8); 1.8024 (1.1); 1.2075 (1.2); 1.1973 (2.8); 1.1882 (2.8); 1.1775 (1.0); −0.0002 (0.8) I.160: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.5860 (2.1); 7.8057 (0.7); 7.7947 (0.7); 3.3583 (5.0); 3.3531 (7.1); 3.3499 (7.3); 3.3436 (6.1); 3.3398 (6.2); 2.5897 (7.5); 2.5782 (7.5); 2.5210 (0.4); 2.5123 (5.9); 2.5079 (11.7); 2.5033 (15.1); 2.4987 (10.9); 2.4942 (5.2); 2.3850 (16.0); 1.3256 (1.2); 1.3145 (3.0); 1.3061 (3.3); 1.2958 (1.3); 0.9725 (1.3); 0.9621 (3.1); 0.9538 (3.0); 0.9426 (1.1); −0.0002 (1.0) I.161: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7660 (0.5); 8.7493 (0.5); 3.5692 (0.5); 3.5519 (0.5); 3.5461 (0.6); 3.5287 (0.5); 3.3498 (20.2); 2.5099 (11.0); 2.5059 (13.2); 2.5019 (10.1); 2.3840 (6.3); 1.4241 (16.0); 0.4977 (0.3); 0.4550 (0.3); 0.4430 (0.4); 0.3557 (0.4); 0.3436 (0.3) I.162: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2600 (8.0); 6.8961 (1.1); 5.8104 (1.0); 4.3955 (0.6); 4.3826 (0.9); 4.3683 (1.0); 4.3532 (1.0); 4.3407 (0.6); 3.4146 (1.4); 3.4095 (1.6); 3.3956 (2.6); 3.3804 (1.4); 2.9544 (0.6); 2.8829 (0.6); 2.7570 (0.7); 2.7435 (0.8); 2.7359 (0.6); 2.7251 (0.8); 2.7117 (0.8); 2.7009 (0.4); 2.4934 (16.0); 2.0064 (1.4); 1.9950 (2.0); 1.9803 (1.5); 1.9639 (0.6); 1.6663 (0.4); 1.6458 (0.5); 1.6362 (0.6); 1.6243 (0.5); 1.6152 (0.9); 1.6050 (0.5); 1.5937 (0.7); 1.5842 (0.8); 1.5629 (9.0); −0.0002 (9.5) I.163: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.0520 (0.9); 8.0356 (0.9); 7.9776 (0.4); 7.9640 (0.6); 7.9601 (0.6); 7.9476 (0.4); 4.5662 (0.5); 4.5499 (0.5); 4.5405 (0.5); 4.5241 (0.5); 3.3410 (30.7); 3.2225 (0.5); 3.2116 (0.4); 3.1955 (0.4); 3.1834 (0.3); 3.0995 (0.4); 3.0811 (0.3); 2.8916 (0.5); 2.7326 (0.4); 2.7313 (0.4); 2.5261 (0.4); 2.5214 (0.6); 2.5127 (8.1); 2.5082 (16.4); 2.5036 (21.3); 2.4989 (15.3); 2.4943 (7.2); 2.4263 (16.0); 1.9226 (1.0); 1.8951 (1.1); 1.7579 (0.4); 1.7489 (0.4); 1.6982 (0.3); 1.6624 (0.3); 1.5134 (0.6); 1.4862 (0.4); 1.4836 (0.4); 1.2437 (0.4); 1.2091 (0.4) I.164: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.5251 (0.9); 9.5035 (0.9); 5.5989 (0.7); 5.5777 (1.1); 5.5564 (0.8); 4.2638 (0.6); 4.2578 (0.6); 4.2460 (1.9); 4.2401 (1.9); 4.2282 (1.9); 4.2224 (1.8); 4.2104 (0.6); 4.2047 (0.6); 3.3487 (31.1); 2.5289 (0.4); 2.5243 (0.6); 2.5155 (6.6); 2.5110 (13.4); 2.5064 (17.6); 2.5018 (12.8); 2.4972 (6.1); 2.3916 (16.0); 1.2476 (4.4); 1.2298 (9.2); 1.2120 (4.2) I.165: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 9.3293 (1.1); 9.3119 (1.1); 7.5578 (1.7); 7.5547 (1.8); 7.5450 (1.8); 7.5419 (1.8); 7.1835 (1.1); 7.1811 (1.5); 7.1787 (1.1); 7.1747 (1.2); 7.1724 (1.7); 7.1700 (1.2); 7.0468 (1.8); 7.0379 (1.7); 7.0340 (1.8); 7.0251 (1.6); 5.8396 (1.8); 5.8223 (1.8); 3.7116 (15.3); 3.3525 (47.8); 2.8949 (0.6); 2.7354 (0.5); 2.5296 (0.5); 2.5248 (0.8); 2.5162 (9.5); 2.5118 (18.6); 2.5072 (24.2); 2.5026 (17.5); 2.4981 (8.4); 2.3946 (16.0) I.166: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.4050 (2.1); 7.3232 (0.5); 7.3190 (0.9); 7.3149 (0.4); 7.3021 (2.6); 7.2980 (1.4); 7.2838 (2.5); 7.2710 (0.7); 7.2673 (1.4); 7.2637 (0.9); 7.2562 (0.4); 7.2498 (1.4); 7.2314 (0.3); 7.1230 (2.0); 7.1192 (2.6); 7.1025 (2.2); 3.6327 (15.8); 3.3976 (1.5); 3.3572 (51.1); 3.0607 (1.7); 3.0275 (1.4); 2.8948 (2.4); 2.7360 (2.0); 2.7350 (1.9); 2.5295 (0.5); 2.5248 (0.7); 2.5162 (8.1); 2.5117 (16.0); 2.5071 (20.7); 2.5025 (14.9); 2.4980 (7.1); 2.2631 (16.0); 1.3412 (9.0) I.167: ¹H-NMR(400.2 MHz, d₆-DMSO): δ = 8.7344 (0.7); 8.7148 (0.7); 4.7756 (0.4); 4.7527 (0.6); 4.7485 (0.5); 4.7325 (0.5); 4.7283 (0.6); 4.7055 (0.4); 4.4249 (0.4); 4.4206 (0.4); 4.4028 (1.1); 4.3984 (1.0); 4.3807 (0.6); 4.3763 (0.5); 4.2976 (0.5); 4.2812 (0.7); 4.2758 (0.5); 4.2714 (0.7); 4.2593 (0.5); 4.2549 (0.6); 4.2496 (0.6); 4.2332 (0.4); 3.3596 (63.0); 2.5270 (0.4); 2.5222 (0.7); 2.5136 (7.6); 2.5091 (15.2); 2.5045 (19.8); 2.4999 (14.3); 2.4953 (6.8); 2.4848 (0.4); 2.4794 (0.4); 2.4711 (0.5); 2.4664 (0.4); 2.4617 (0.3); 2.4547 (0.4); 2.4486 (0.4); 2.4434 (0.4); 2.4314 (0.3); 2.4021 (16.0); 2.3406 (0.4); 2.3366 (0.6); 2.3137 (0.6); 2.3102 (0.6); 2.3069 (0.5); 2.2867 (0.4); 2.2838 (0.4) I.168: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2598 (9.9); 4.5659 (0.3); 4.2572 (1.4); 4.2393 (4.6); 4.2289 (10.3); 4.2219 (5.6); 4.2037 (1.6); 4.1269 (0.4); 2.9514 (0.4); 2.9417 (0.8); 2.9336 (1.0); 2.9245 (1.5); 2.9151 (1.0); 2.9073 (0.8); 2.8974 (0.4); 2.3150 (16.0); 1.5437 (16.6); 1.3212 (4.3); 1.3034 (8.5); 1.2855 (4.4); 1.2724 (0.6); 0.7770 (0.5); 0.7594 (2.5); 0.7440 (2.5); 0.7291 (1.0); 0.7084 (0.5); 0.6988 (0.4); 0.6911 (0.4); 0.6692 (1.0); 0.6576 (2.8); 0.6507 (3.0); 0.6292 (0.6); −0.0002 (12.1) I.169: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2615 (8.6); 5.6439 (2.1); 3.0923 (1.3); 3.0614 (2.7); 3.0308 (1.7); 3.0280 (1.7); 2.8005 (2.2); 2.7683 (2.2); 2.7288 (2.2); 2.6909 (1.8); 2.5472 (16.0); 2.0959 (1.4); 2.0894 (1.5); 2.0625 (2.7); 2.0447 (1.0); 2.0347 (1.5); 2.0294 (1.4); 1.5633 (4.2); 1.2587 (0.4); −0.0002 (11.9) I.170: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.3450 (1.5); 7.3264 (3.9); 7.3081 (3.3); 7.2587 (26.7); 7.2371 (5.0); 5.7338 (2.6); 5.2977 (0.4); 2.7816 (2.4); 2.7505 (2.6); 2.6027 (1.1); 2.5627 (16.0); 2.0481 (3.2); 2.0300 (5.6); 2.0010 (1.6); 1.9687 (0.4); 1.7790 (1.2); 1.7483 (1.9); 1.7363 (1.7); 1.7060 (1.0); 1.5359 (28.6); 1.2561 (0.7); −0.0002 (29.1) I.171: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2620 (3.8); 6.4718 (1.4); 3.8185 (16.0); 2.7063 (0.6); 2.6841 (1.2); 2.6734 (1.7); 2.6562 (2.5); 2.6373 (1.6); 2.6266 (1.5); 2.6044 (2.6); 2.5822 (1.8); 2.5769 (1.6); 2.5506 (0.8); 2.4842 (15.7); 2.1644 (0.6); 2.1597 (0.5); 2.1442 (1.8); 2.1352 (1.0); 2.1242 (2.5); 2.1037 (1.8); 2.0826 (0.6); 2.0055 (1.9); 1.5661 (5.5); 1.2655 (0.8); 0.8820 (0.6); 0.8648 (0.3); 0.0701 (1.7); −0.0002 (5.2) I.172: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 10.3084 (0.9); 4.4101 (4.4); 3.3265 (14.2); 2.5098 (11.2); 2.3803 (16.0) I.173: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 10.3829 (1.3); 10.3667 (1.4); 7.9612 (2.8); 4.9479 (1.1); 4.9302 (1.6); 4.9124 (1.2); 3.6991 (0.4); 3.3271 (44.5); 3.1599 (0.6); 3.0681 (0.4); 2.8997 (14.2); 2.7405 (13.3); 2.5100 (15.0); 2.4320 (0.9); 2.3876 (16.0); 1.4918 (7.6); 1.4736 (7.8); 1.3792 (0.4); 1.3613 (0.4) I.174: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.4072 (1.6); 3.3172 (3.8); 2.5008 (6.1); 2.3591 (9.6); 1.9882 (0.6); 1.4310 (16.0); 1.1745 (0.4); −0.0002 (2.0) I.175: ¹H-NMR(400.1 MHz, CDCl3): δ = 17.1997 (0.7); 13.6163 (8.8); 8.8025 (0.7); 8.7847 (0.8); 8.3654 (0.4); 8.0723 (16.0); 7.3244 (1.9); 7.3061 (4.4); 7.2917 (4.0); 7.2684 (22.0); 7.2643 (28.0); 7.2601 (23.0); 7.2145 (1.2); 7.1948 (0.8); 7.1784 (0.7); 7.1476 (51.8); 7.0721 (2.7); 7.0507 (5.9); 7.0209 (5.1); 6.9977 (2.8); 6.9839 (1.0); 6.9465 (0.4); 6.8676 (0.4); 6.7515 (3.2); 6.7382 (1.8); 6.7187 (5.4); 6.6986 (7.7); 6.6787 (4.7); 6.6593 (1.6); 6.5239 (0.5); 6.1197 (0.7); 5.9872 (0.6); 5.9705 (0.7); 5.9565 (1.0); 5.9388 (1.8); 5.9209 (1.0); 4.7637 (14.4) I.176: ¹H-NMR(400.1 MHz, CDCl3): δ = 7.2597 (6.6); 6.5686 (0.6); 3.7962 (8.9); 2.4755 (8.6); 1.6725 (16.0); 1.5408 (7.4); −0.0002 (9.0) I.177: ¹H-NMR(400.1 MHz, d₆-DMSO): δ = 8.7944 (16.0); 3.3594 (7.9); 3.3451 (1.0); 3.3272 (10.2); 3.3118 (100.3); 3.2877 (1.3); 3.2761 (0.6); 2.9870 (11.7); 2.9535 (10.0); 2.6694 (0.5); 2.6204 (0.7); 2.6013 (9.3); 2.5898 (14.1); 2.5751 (10.3); 2.5505 (0.8); 2.5050 (53.9); 2.5006 (73.8); 2.4962 (56.3); 2.4618 (1.0); 2.4547 (1.0); 2.4392 (105.2); 2.4014 (0.7); 2.3839 (0.3); 2.3322 (0.5); 2.2744 (0.7); 2.2524 (2.7); 2.2365 (3.2); 2.2143 (3.9); 2.0440 (3.0); 2.0280 (3.5); 2.0127 (3.5); 2.0018 (4.4); 1.9704 (5.4); 1.9392 (4.1); 1.9150 (2.8); 1.9064 (2.7); 1.8993 (3.3); 1.8830 (3.0); 1.8734 (2.6); 1.8668 (2.2); 1.8583 (1.7); 1.8390 (0.8); 0.1459 (0.4); 0.0151 (0.3); 0.0078 (3.5); −0.0002 (96.8); −0.0346 (0.4); −0.1495 (0.4)

Biological Data

Example A described below show the induction of defence gene expression in Arabidopsis thaliana by compounds according to formula (I), specifically the stimulation of the salicylic acid pathway. Therefore, these compounds could induce host defenses and thus protect plants against a wide range of pathogens including bacteria and fungi.

Examples B, C, D, E and F described below show the in vivo activity of compounds in planta according to formula (I) by stimulating the plant defense against various pathogens infecting plants including bacteria and fungi.

Examples G, H, I and J described below show the in vitro cell test direct inactivity of compounds according to formula (I) against various pathogens including bacteria and fungi, thus illustrating the mode of action of compounds according to formula (I) as plant host defence inducers.

Examples K, L, M, N and O described below show in vivo activity in planta of comparative compounds, CMP1, CMP2, CMP3, CMP4, CMP5, CMP6 and CMP7 prepared in accordance with the teaching of WO2004/024692 and of compounds according to the present invention.

A comparison of the activity of CMP1, CMP2, CMP3, CMP4, CMP5, CMP6 and CMP7 with that of the compounds of the present invention shows that these prior art compounds are clearly less active and thus do not provide the beneficial technical effect of the inventive compounds.

Examples P, Q, R, S and T described below show in vivo activity in planta of comparative compounds, CMP8, CMP9, CMP10, CMP11, CMP12, CMP13, CMP14, CMP15 and CMP16 prepared in accordance with the teaching of EP0450355 and of compounds according to the present invention.

A comparison of the activity of CMP8, CMP9, CMP10, CMP11, CMP12, CMP13, CMP14, CMP15 and CMP16 with that of the compounds of the present invention shows that these prior art compounds are clearly less active and thus do not provide the beneficial technical effect of the inventive compounds.

Example A: Induction of Defense Gene Expression in Arabidopsis thaliana

Arabidopsis thaliana reporter plants containing the coding sequence of a green fluorescent protein (GFP) linked to the salicylate responsive promoter sequence of the PR1 (pathogenesis-related protein I) gene (AT2G14610) were grown for five days and then sprayed with compounds. On the 3rd day after spraying, plant fluorescence was assessed with a MacroFluo instrument from Leica Microsystems (Wetzlar, Germany). Fluorescences were quantified with the Meta-Morph Microscopy Automation & Image Analysis Software (Molecular Devices, Sunnyvale, Calif., United States). Background fluorescence in mock treated leaves was set as 1.00. Salicylic acid treatment (300 ppm) resulted in a relative fluorescence value of 2.70, proving the validity of the test system.

In this test, the following compounds according to the invention showed a relative fluorescence value at least above 2 at a concentration of 300 ppm of compound: I.001; I.002; I.004; I.006; I.007; I.008; I.009; I.010; I.012; I.013; I.014; I.015; I.016; I.018; I.019; I.021; I.022; I.023; I.025; I.026; I.031; I.032; I.033; I.034; I.035; I.036; I.037; I.038; I.039; I.040; I.041; I.042; I.043; I.044; I.045; I.047; I.048; I.049; I.050; I.052; I.053; I.054; I.055; I.060; I.061; I.062; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.076; I.077; I.078; I.079; I.080; I.081; I.083; I.084; I.085; I.087; I.088; I.089; I.090; I.091; I.092; I.094; I.095; I.099; I.100; I.101; I.102; I.103; I.104; I.105; I.108; I.110; I.113; I.114; I.115; I.116; I.117; I.118; I.119; I.120; I.121; I.122; I.123; I.124; I.125; I.126; I.127; I.128; I.129; I.131; I.132; I.133; I.134; I.135; I.136; I.137; I.149; I.150; I.154; I.155; I.157; I.158; I.159; I.161; I.162; I.164; I.165; I.167; I.168; I.169; I.171; I.172; I.173; I.174; I.175; I.176.

In this test, the following compounds according to the invention showed a relative fluorescence value at least above 2 at a concentration of 75 ppm of compound: I.002; I.003; I.004; I.006; I.008; I.009; I.014; I.015; I.016; I.018; I.019; I.021; I.024; I.025; I.026; I.031; I.032; I.039; I.040; I.044; I.049; I.050; I.053; I.055; I.060; I.067; I.068; I.071; I.072; I.077; I.080; I.081; I.089; I.091; I.094; I.095; I.100; I.102; I.104; I.105; I.108; I.110; I.113; I.115; I.118; I.119; I.122; I.123; I.124; I.125; I.127; I.128; I.129; I.131; I.132; I.133; I.134; I.136; I.137; I.150; I.154; I.155; I.157; I.158; I.161; I.164; I.171; I.172; I.173; I.174; I.175; I.176.

Salicylate is a major defence hormone against plant pathogens. All the compounds described above stimulate the salicylic acid pathway and therefore could protect plants against a wide range of pathogens.

Example B: In Vivo Preventive Test on Colletotrichum lindemuthianum (Anthracnose on Bean)

The tested active ingredients were prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.

The young plants of bean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.

After 72 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Colletotrichum lindemuthianum spores. The contaminated bean plants were incubated for 24 hours at 20° C. and at 100% relative humidity and then for 5 days at 20° C. and at 90% relative humidity.

The test was evaluated 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I.006; I.021; I.032; I.038; I.072; I.078; I.080; I.127; I.132.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I.003; I.045; I.071; I.081; I.122; I.131; I.136.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I.013; I.014; I.023; I.031; I.033; I.039; I.040; I.041; I.042; I.043; I.044; I.047; I.077; I.083; I.099; I.101; I.108; I.137; I.173.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 31 ppm of active ingredient: I.014.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 31 ppm of active ingredient: I.042; I.044; I.077; I.099; I.165.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 31 ppm of active ingredient: I.023; I.041; I.043; I.047.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 125 ppm of active ingredient: I.021; I.095; I.115; I.122; I.175.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 125 ppm of active ingredient: I.013; I.014; I.033; I.042; I.060; I.077; I.099; I.108; I.165; I.167; I.172.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 125 ppm of active ingredient: I.023; I.040; I.041; I.043; I.044; I.047.

Example C: In Vivo Preventive Test on Peronospora parasitica (Crucifer Downy Mildew)

The tested active ingredients were prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.

The young plants of cabbage were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.

After 72 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Peronospora parasitica spores. The contaminated cabbage plants were incubated for 5 days at 20° C. and at 100% relative humidity.

The test was evaluated 5 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I.059; I.098.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I.022; I.033; I.035; I.134.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I.003; I.006; I.007; I.008; I.014; I.015; I.016; I.021; I.023; I.031; I.032; I.039; I.040; I.041; I.042; I.043; I.044; I.045; I.047; I.049; I.056; I.057; I.058; I.060; I.070; I.071; I.072; I.076; I.077; I.078; I.079; I.080; I.081; I.083; I.095; I.099; I.101; I.108; I.122; I.127; I.128; I.131; I.132; I.133; I.136; I.137; I.173.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 31 ppm of active ingredient: I.008; I.021; I.038; I.070; I.071; I.108; I.133; I.137; I.173; I.176.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 31 ppm of active ingredient: I.001; I.002; I.006; I.023; I.032; I.077; I.078; I.079; I.081; I.095; I.101; I.131; I.132; I.136.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 31 ppm of active ingredient: I.014; I.015; I.016; I.039; I.042; I.043; I.044; I.045; I.047; I.049; I.060; I.083; I.099; I.122; I.162; I.164; I.165; I.167; I.171; I.172; I.175.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 125 ppm of active ingredient: I.022; I.033; I.035; I.108; I.110; I.163.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 125 ppm of active ingredient: I.003; I.056; I.071; I.072; I.101; I.132.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 125 ppm of active ingredient: I.006; I.008; I.014; I.015; I.016; I.021; I.023; I.031; I.032; I.039; I.041; I.042; I.043; I.044; I.045; I.047; I.049; I.060; I.070; I.076; I.077; I.078; I.079; I.080; I.081; I.083; I.095; I.098; I.099; I.115; I.122; I.127; I.128; I.131; I.133; I.136; I.137; I.162; I.164; I.165; I.167; I.171; I.172; I.173; I.174; I.175; I.176.

Example D: In Vivo Preventive Test on Xanthomonas campestris pv. Campestris (Black Rot on Cabbage)

The tested active ingredients were prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.

The young plants of cabbage were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.

After 72 hours, the plants were contaminated by spraying the leaves with an aqueous bacteria suspension of Xanthomonas campestris pv. campestris. The contaminated cabbage plants were incubated for 8 or 10 days at 27° C. at 95% relative humidity.

The test was evaluated 8 or 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: 1.023.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I.006; I.034; I.049; I.060; I.127.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I.032; I.080; I.095; I.097; I.122; I.137.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 31 ppm of active ingredient: I.033; I.039; I.044; I.070; I.076; I.078; I.079; I.080; I.095; I.167; I.175.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 31 ppm of active ingredient: I.049; I.077; I.081; I.127; I.164; I.172.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 31 ppm of active ingredient: I.032; I.122.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 125 ppm of active ingredient: I.033; I.039; I.060; I.071; I.171; I.174.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 125 ppm of active ingredient: I.009; I.023; I.035; I.042; I.044; I.047; I.070; I.077; I.080; I.173; I.175.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 125 ppm of active ingredient: I.032; I.081; I.095; I.122; I.127; I.137.

Example E: In Vivo Preventive Test on Uromyces appendiculatus (Bean Rust)

The tested active ingredients were prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.

The young plants of bean were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.

After 72 hours, the plants were contaminated by spraying the leaves with an aqueous suspension of Uromyces appendiculatus spores. The contaminated bean plants were incubated for 24 hours at 20° C. and at 100% relative humidity and then for 9 days at 20° C. and at 70-80% relative humidity.

The test was evaluated 10 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I.010; I.013; I.022; I.031; I.038.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I.007; I.016; I.021; I.035; I.039; I.049; I.078; I.079.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 500 ppm of active ingredient: I.003; I.005; I.006; I.008; I.009; I.014; I.015; I.032; I.033; I.034; I.042; I.043; I.044; I.045; I.047; I.060; I.070; I.071; I.072; I.076; I.077; I.080; I.081; I.083; I.095; I.097; I.099; I.101; I.108; I.122; I.127; I.128; I.131; I.132; I.133; I.134; I.136; I.137; I.168; I.173.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 31 ppm of active ingredient: I.013; I.049; I.077.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 31 ppm of active ingredient: I.009; I.042; I.047; I.095; I.171.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 31 ppm of active ingredient: I.006; I.014; I.015; I.016; I.032; I.044; I.060; I.083; I.132; I.133; I.136; I.163; I.164; I.165; I.167; I.174; I.176.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 125 ppm of active ingredient: I.175.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 125 ppm of active ingredient: I.006; I.009; I.013; I.035; I.043; I.076; I.173.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 125 ppm of active ingredient: I.003; I.008; I.014; I.016; I.032; I.042; I.044; I.047; I.049; I.060; I.077; I.081; I.083; I.095; I.099; I.108; I.110; I.115; I.127; I.131; I.132; I.133; I.136; I.137; I.162; I.163; I.164; I.165; I.167; I.171; I.172; I.174; I.176.

Example F: In Vivo Preventive Test on Pseudomonas syringae pv. Tomato (Bacterial Speck on Tomato)

The tested active ingredients were prepared by homogenization in a mixture of acetone/Dimethyl sulfoxide/Tween®, and then diluted with water to obtain the desired active material concentration.

The young plants of tomato were treated by spraying the active ingredient prepared as described above. Control plants were treated only with an aqueous solution of acetone/Dimethyl sulfoxide/Tween®.

After 72 hours, the plants were contaminated by spraying the leaves with an aqueous bacteria suspension of Pseudomonas syringae pv. tomato. The contaminated tomato plants were incubated for 4 days in saturated atmosphere at 22° C. day/20° C. night−70% HR and then for 1 or 2 days at 22° C. day/20° C. night at 70-80% relative humidity.

The test was evaluated 5 or 6 days after the inoculation. 0% means an efficacy which corresponds to that of the control plants while an efficacy of 100% means that no disease was observed.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 500 ppm of active ingredient: I.032; I.042; I.059; I.060; I.079; I.080; I.101; I.108; I.127; I.128; I.137.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 500 ppm of active ingredient: I.058; I.077; I.078; I.095; I.122.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 31 ppm of active ingredient: I.047; I.099; I.122.

In this test the following compounds according to the invention showed efficacy between 70% and 79% at a concentration of 125 ppm of active ingredient: I.042; I.081; I.083; I.095; I.176.

In this test the following compounds according to the invention showed efficacy between 80% and 89% at a concentration of 125 ppm of active ingredient: I.099; I.115; I.122; I.165; I.167.

In this test the following compounds according to the invention showed efficacy between 90% and 100% at a concentration of 125 ppm of active ingredient: I.010; I.047; I.172.

Example G: Alternaria alternata In Vitro Cell Test

Solvent: DMSO

Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g Mycological Peptone (Oxoid), 1.4 g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spores suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was ≤□1%.

A spore suspension of A. alternata was prepared and diluted to the desired spore density.

Fungicides were evaluated for their ability to inhibit spore germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 5 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed no direct activity (efficacy lower than or equal to 30%) at a concentration of 5 ppm of active ingredient: I.001; I.002; I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.012; I.013; I.014; I.015; I.016; I.017; I.018; I.019; I.020; I.021; I.022; I.023; I.024; I.025; I.026; I.027; I.028; I.029; I.030; I.031; I.032; I.033; I.034; I.035; I.037; I.038; I.039; I.041; I.042; I.043; I.044; I.045; I.047; I.048; I.049; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.075; I.076; I.077; I.078; I.079; I.080; I.081; I.082; I.083; I.084; I.085; I.086; I.087; I.088; I.089; I.090; I.091; I.092; I.093; I.094; I.095; I.097; I.098; I.101; I.102; I.103; I.104; I.105; I.106; I.107; I.108; I.109; I.110; I.113; I.114; I.115; I.116; I.117; I.118; I.119; I.120; I.121; I.122; I.123; I.124; I.125; I.126; I.136; I.139; I.149; I.150; I.152; I.162; I.163; I.164; I.165; I.166; I.167; I.171; I.174; I.175; I.176.

In this test, the following compounds according to the invention showed no direct activity (efficacy lower than or equal to 30%) at a concentration 20 ppm of active ingredient: I.002; I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.012; I.014; I.016; I.017; I.018; I.019; I.020; I.022; I.023; I.024; I.025; I.027; I.029; I.030; I.031; I.032; I.033; I.034; I.038; I.039; I.041; I.042; I.043; I.045; I.047; I.048; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.074; I.075; I.076; I.077; I.078; I.080; I.081; I.082; I.083; I.084; I.085; I.086; I.087; I.089; I.091; I.092; I.093; I.094; I.095; I.098; I.102; I.103; I.104; I.105; I.106; I.107; I.108; I.110; I.114; I.115; I.118; I.119; I.120; I.122; I.123; I.124; I.125; I.136; I.139; I.152; I.162; I.164; I.165; I.167; I.171; I.174; I.175; I.176.

Example H: Colletotrichum lindemuthianum In Vitro Cell Test

Solvent: DMSO

Culture medium: 14.6 g anhydrous D-glucose (VWR), 7.1 g Mycological Peptone (Oxoid), 1.4 g granulated Yeast Extract (Merck), QSP 1 liter

Inoculum: spores suspension

Fungicides were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was ≤□1%.

A spore suspension of C. lindemuthianum was prepared and diluted to the desired spore density. Fungicides were evaluated for their ability to inhibit spores germination and mycelium growth in liquid culture assay. The compounds were added in the desired concentration to the culture medium with spores. After 6 days incubation, fungi-toxicity of compounds was determined by spectrometric measurement of mycelium growth. Inhibition of fungal growth was determined by comparing the absorbance values in wells containing the fungicides with the absorbance in control wells without fungicides.

In this test, the following compounds according to the invention showed no direct activity (efficacy lower than or equal to 30%) at a concentration of 5 ppm of active ingredient: I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.012; I.013; I.014; I.015; I.016; I.017; I.018; I.019; I.020; I.021; I.022; I.023; I.024; I.025; I.026; I.027; I.029; I.030; I.031; I.032; I.033; I.034; I.035; I.036; I.037; I.038; I.039; I.041; I.042; I.043; I.044; I.045; I.047; I.048; I.049; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.075; I.076; I.077; I.078; I.079; I.080; I.081; I.082; I.083; I.084; I.085; I.086; I.087; I.088; I.089; I.090; I.091; I.092; I.093; I.094; I.095; I.097; I.098; I.100; I.101; I.102; I.103; I.104; I.105; I.106; I.107; I.109; I.110; I.113; I.114; I.115; I.116; I.117; I.118; I.119; I.120; I.121; I.122; I.123; I.124; I.125; I.126; I.136; I.139; I.149; I.150; I.152; I.162; I.163; I.164; I.165; I.166; I.167; I.171; I.174; I.175; I.176.

In this test, the following compounds according to the invention showed no direct activity (efficacy lower than or equal to 30%) at a concentration of 20 ppm of active ingredient: I.004; I.007; I.008; I.009; I.010; I.012; I.014; I.015; I.016; I.018; I.019; I.022; I.023; I.024; I.025; I.027; I.029; I.030; I.031; I.033; I.035; I.039; I.045; I.051; I.052; I.053; I.054; I.055; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.075; I.076; I.077; I.078; I.079; I.080; I.081; I.082; I.084; I.085; I.087; I.088; I.090; I.091; I.092; I.093; I.094; I.095; I.097; I.098; I.101; I.102; I.103; I.104; I.105; I.107; I.109; I.110; I.115; I.117; I.118; I.119; I.120; I.122; I.123; I.124; I.125; I.126; I.136; I.139; I.162; I.163; I.164; I.174; I.175.

Example I: Xanthomonas campestris pv. Campestris In Vitro Cell Test

Solvent: DMSO

Culture medium: LB broth medium (Luria Broth Miller) Sigma

Inoculum: bacteria suspension

Compounds were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was ≤1%.

Inoculum was prepared from a pre-culture of bacteria grown in liquid medium and diluted to the desired optical density (OD).

Compounds were evaluated for their ability to inhibit bacteria growth in liquid culture assay. The compounds were added in the desired concentrations to culture medium containing the bacteria suspension. After 24 h of incubation, the efficacy of compounds was determined by spectrometric measurement of bacteria growth. Inhibition was determined by comparing the absorbance values in wells containing the compounds with the absorbance in control wells without active ingredients.

In this test, the following compounds according to the invention showed no direct activity (efficacy lower than or equal to 30%) at a concentration of 5 ppm of active ingredient: I.001; I.002; I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.012; I.013; I.014; I.015; I.016; I.017; I.018; I.019; I.020; I.021; I.022; I.023; I.024; I.025; I.026; I.027; I.028; I.029; I.030; I.031; I.032; I.033; I.034; I.035; I.036; I.037; I.038; I.039; I.040; I.041; I.042; I.043; I.044; I.045; I.047; I.048; I.049; I.050; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.075; I.076; I.077; I.078; I.079; I.080; I.081; I.082; I.083; I.084; I.085; I.086; I.087; I.088; I.089; I.090; I.091; I.092; I.093; I.094; I.095; I.097; I.098; I.099; I.100; I.101; I.102; I.103; I.104; I.105; I.106; I.107; I.108; I.109; I.110; I.113; I.114; I.115; I.116; I.117; I.118; I.119; I.120; I.121; I.122; I.123; I.124; I.125; I.126; I.136; I.139; I.149; I.150; I.152; I.162; I.163; I.164; I.165; I.166; I.167; I.171; I.174; I.175; I.176.

In this test, the following compounds according to the invention showed no direct activity (efficacy lower than or equal to 30%) at a concentration of 20 ppm of active ingredient: I.001; I.002; I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.012; I.014; I.015; I.016; I.017; I.018; I.019; I.020; I.021; I.022; I.023; I.024; I.025; I.026; I.027; I.028; I.029; I.030; I.031; I.033; I.034; I.035; I.036; I.037; I.038; I.039; I.040; I.041; I.042; I.043; I.044; I.045; I.047; I.048; I.049; I.050; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.075; I.076; I.077; I.078; I.079; I.080; I.081; I.082; I.083; I.084; I.085; I.086; I.087; I.088; I.089; I.090; I.091; I.092; I.093; I.094; I.095; I.097; I.098; I.100; I.101; I.102; I.103; I.104; I.105; I.106; I.107; I.108; I.109; I.110; I.113; I.114; I.115; I.116; I.117; I.118; I.119; I.120; I.121; I.122; I.123; I.124; I.125; I.126; I.136; I.139; I.149; I.150; I.152; I.162; I.163; I.164; I.165; I.166; I.167; I.171; I.174; I.175; I.176.

Example J: Pseudomonas syringae pv. Tomato In Vitro Cell Test

Solvent: DMSO

Culture medium: LB broth medium (Luria Broth Miller) Sigma

Inoculum: bacteria suspension

Compounds were solubilized in DMSO and the solution used to prepare the required range of concentrations. The final concentration of DMSO used in the assay was ≤1%.

Inoculum was prepared from a pre-culture of bacteria grown in liquid medium and diluted to the desired optical density (OD).

Compounds were evaluated for their ability to inhibit bacteria growth in liquid culture assay. The compounds were added in the desired concentrations to culture medium containing the bacteria suspension. After 24 h of incubation, the efficacy of compounds was determined by spectrometric measurement of bacteria growth. Inhibition was determined by comparing the absorbance values in wells containing the compounds with the absorbance in control wells without active ingredients.

In this test, the following compounds according to the invention showed no direct activity (efficacy lower than or equal to 30%) at a concentration of 20 ppm of active ingredient: I.001; I.002; I.003; I.004; I.005; I.006; I.007; I.008; I.009; I.010; I.012; I.013; I.014; I.015; I.016; I.017; I.018; I.019; I.020; I.021; I.022; I.023; I.024; I.025; I.026; I.027; I.028; I.029; I.030; I.031; I.032; I.033; I.034; I.035; I.036; I.037; I.038; I.039; I.040; I.041; I.042; I.043; I.044; I.045; I.047; I.048; I.049; I.050; I.051; I.052; I.053; I.054; I.055; I.056; I.057; I.058; I.059; I.060; I.061; I.062; I.063; I.064; I.065; I.066; I.067; I.068; I.069; I.070; I.071; I.072; I.073; I.074; I.075; I.076; I.077; I.078; I.079; I.080; I.081; I.082; I.083; I.084; I.085; I.086; I.087; I.088; I.089; I.090; I.091; I.092; I.093; I.094; I.095; I.097; I.098; I.099; I.100; I.101; I.102; I.103; I.104; I.105; I.106; I.107; I.108; I.109; I.110; I.113; I.114; I.115; I.116; I.117; I.118; I.119; I.120; I.121; I.122; I.123; I.124; I.125; I.126; I.136; I.139; I.149; I.150; I.152; I.162; I.163; I.164; I.165; I.166; I.167; I.171; I.174; I.175; I.176.

Example K: Comparative Examples

Compounds CMP1, CMP2, CMP3 and CMP4 were tested in an in vivo preventive test on Xanthomonas campestris pv. campestris (black rot on cabbage) in the same conditions as described in Example D.

Compounds CMP1, CMP2, CMP3 and CMP4 were prepared in accordance with the teaching of WO2004/024692.

The results are as shown in the table below.

Efficacy (%) Efficacy (%) Ex. Structure at 500 ppm at 31 ppm CMP1

 0*  10* CMP2

0 0 CMP3

0  38 CMP4

0 0 *arithmetic mean of 2 tests

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP1.

Ex. Structure I.076

I.137

I.080

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP1 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.080; I.137 were shown to exhibit an efficacy of at least 90% whereas CMP1 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP1 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compounds I.076; I.080 were shown to exhibit an efficacy of at least 70% whereas CMP1 was shown to exhibit an efficacy of 10% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP2.

Ex. Structure I.006

I.034

I.077

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP2 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.006; I.034 were shown to exhibit an efficacy of at least 80% whereas CMP2 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP2 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compound I.077 was shown to exhibit an efficacy of at least 80% whereas CMP2 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP3.

Ex. Structure I.060

I.070

I.095

I.175

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP3 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.060; I.095 were shown to exhibit an efficacy of at least 80% whereas CMP3 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP3 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compounds I.070; I.095; I.175 were shown to exhibit an efficacy of at least 70% whereas CMP3 was shown to exhibit an efficacy below 40% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP4.

Ex. Structure I.078

I.079

I.081

I.122

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP4 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compounds I.078; I.081; I.079; I.122 were shown to exhibit an efficacy of at least 70% whereas CMP4 was shown to exhibit no efficacy at the same concentration.

Example L: Comparative Examples

Compounds CMP1 and CMP2 were tested in an in vivo preventive test on Pseudomonas syringae pv. tomato (bacterial speck on tomato) the same conditions as described in Example F.

Compounds CMP1 and CMP2 were prepared in accordance with the teaching of WO2004/024692. The results are as shown in the table below.

Efficacy (%) Ex. Structure at 500 ppm CMP1

 0 CMP2

31

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP1.

Ex. Structure I.137

I.080

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP1 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.080; I.137 were shown to exhibit an efficacy of at least 70% whereas CMP1 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP2.

Ex. Structure I.077

I.128

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP2 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.077; I.128 were shown to exhibit an efficacy of at least 70% whereas CMP2 was shown to exhibit an efficacy below 40% at the same concentration.

Example M: Comparative Examples

Compounds CMP2, CMP4, CMP5 and CMP6 were tested in an in vivo preventive test on Colletotrichum lindemuthianum (Anthracnose on bean) in the same conditions as described in Example B.

Compounds CMP2, CMP4, CMP5 and CMP6 were prepared in accordance with the teaching of WO2004/024692.

The results are as shown in the table below.

Efficacy (%) Ex. Structure at 500 ppm CMP2

0

Efficacy (%) Ex. Structure at 125 ppm CMP2

0 CMP4

35 CMP5

0

Efficacy (%) Ex. Structure at 31 ppm CMP4

0 CMP6

35

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP2.

Ex. Structure Ex. Structure 1.006

1.014

1.077

1.132

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP2 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.006; I.014; I.077; I.132 were shown to exhibit an efficacy of at least 70% whereas CMP2 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP2 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compounds I.014; I.077 were shown to exhibit an efficacy of at least 80% whereas CMP2 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP4.

Ex. Structure Ex. Structure 1.043

1.122

1.165

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP4 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compounds I.043; I.122; I.165 were shown to exhibit an efficacy of at least 80% whereas CMP4 was shown to exhibit an efficacy below 40% at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP4 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compounds I.043; I.122; I.165 were shown to exhibit an efficacy of at least 70% whereas CMP4 was shown to exhibit no efficacy at the same concentration

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP5.

Ex. Structure Ex. Structure 1.033

1.108

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP5 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compounds I.033; I.108 were shown to exhibit an efficacy of at least 80% whereas CMP5 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP6.

Ex. Structure Ex. Structure 1.044

1.047

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP6 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compounds I.044; I.047 were shown to exhibit an efficacy of at least 80% whereas CMP6 was shown to exhibit an efficacy below 40% at the same concentration.

Example N: Comparative Examples

Compounds CMP2, CMP4 and CMP5 were tested in an in vivo preventive test on Uromyces appendiculatus (bean rust) in the same conditions as described in Example E.

Compounds CMP2, CMP4 and CMP5 were prepared in accordance with the teaching of WO2004/024692.

The results are as shown in the tables below.

Efficacy (%) Ex. Structure at 500 ppm CMP2

28* CMP5

17 *arithmetic mean of 3 tests

Efficacy (%) Ex. Structure at 31 ppm CMP2

35* CMP4

35 CMP5

0 *arithmetic mean of 2 tests

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP2.

Ex. Structure Ex. Structure 1.006

1.034

1.077

1.014

1.132

1.128

1.016

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP2 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.006; I.014; I.016; I.034; I.077; I.128; I.132 were shown to exhibit an efficacy of at least 80% whereas CMP2 was shown to exhibit an efficacy below 30% at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP2 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compounds I.006; I.014; I.016; I.077; I.132 were shown to exhibit an efficacy of at least 70% whereas CMP2 was shown to exhibit an efficacy below 40% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP5.

Ex. Structure Ex. Structure 1.033

1.003*

1.005

1.015

1.032

1.035

1.101

1.131

1.136

*mixture of stereoisomers

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP5 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.003; I.005; I.015; I.032; I.033; I.035; I.101; I.131; I.136 were shown to exhibit an efficacy of at least 80% whereas CMP5 was shown to exhibit an efficacy below 20% at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP5 when tested at a concentration of 500 ppm. More specifically, at a concentration of 31 ppm, compounds I.015; I.032; I.136 were shown to exhibit an efficacy of at least 90% whereas CMP5 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP4.

Ex. Structure Ex. Structure 1.171

1.176

1.165

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP4 when tested at a concentration of 500 ppm. More specifically, at a concentration of 31 ppm, compounds I.165; I.171; I.176 were shown to exhibit an efficacy of at least 80% whereas CMP4 was shown to exhibit an efficacy below 40% at the same concentration.

Example O: Comparative Examples

Compounds CMP2, CMP3, CMP4, CMP5, CMP6 and CMP7 were tested in an in vivo preventive test on Peronospora parasitica (Crucifer downy mildew) in the same conditions as described in Example C. Compounds CMP2, CMP3, CMP4, CMP5, CMP6 and CMP7 were prepared in accordance with the teaching of WO2004/024692.

The results are as shown in the tables below.

Efficacy (%) Ex. Structure at 500 ppm CMP3

0 CMP4

0 CMP6

0 CMP7

0

Efficacy (%) Ex. Structure at 125 ppm CMP2

25 CMP3

0 CMP4

0 CMP5

38 CMP6

0

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP3.

Ex. Structure Ex. Structure 1.060

1.095

1.174

1.070

1.175

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP3 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.060; I.070; I.095 were shown to exhibit an efficacy of at least 90% whereas CMP3 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP3 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compounds I.060; I.070; I.095; I.174; I.175 were shown to exhibit an efficacy of at least 90% whereas CMP3 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP4.

Ex. Structure I.171

I.176

I.165

I.043

I.122

I.078

I.081

I.079

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP4 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, I.043; I.078; I.079; I.081; I.122 were shown to exhibit an efficacy of at least 90% whereas CMP4 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP4 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compounds I.043; I.078; I.079; I.081; I.122; I.165; I.171; I.176 were shown to exhibit an efficacy of at least 90% whereas CMP4 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP6.

Ex. Structure I.044

I.047

I.045

I.039

I.040

I.049

I.164

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP6 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.039; I.040; I.044; I.045; I.047; I.049 were shown to exhibit an efficacy of at least 90% whereas CMP6 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP6 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.039; I.040; I.044; I.045; I.047; I.049; I.164 were shown to exhibit an efficacy of at least 90% whereas CMP6 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP7.

Ex. Structure I.133

I.134

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP7 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.133; I.134 were shown to exhibit an efficacy of at least 80% whereas CMP7 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP2.

Ex. Structure I.006

I.016

I.077

I.014

I.132

I.128

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP2 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compounds I.006; I.014; I.016; I.077; I.128; I.132 were shown to exhibit an efficacy of at least 80% whereas CMP2 was shown to exhibit an efficacy below 30% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP5.

Ex. Structure I.033

I.003*

I.136

I.015

I.032

I.035

I.101

I.131

*mixture of stereoisomers

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP5 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compounds I.003; I.015; I.032; I.033; I.035; I.101; I.131; I.136 were shown to exhibit an efficacy of at least 70% whereas CMP5 was shown to exhibit an efficacy below 40% at the same concentration.

Example P: Comparative Examples

Compounds CMP8, CMP9 and CMP10 were tested in an in vivo preventive test on Xanthomonas campestris pv. campestris (black rot on cabbage) in the same conditions as described in Example D. Compound CMP8, CMP9 and CMP10 were prepared in accordance with the teaching of EP0450355.

The results are as shown in the tables below.

Efficacy (%) Ex. Structure at 500 ppm CMP8

8 CMP9

0

Efficacy (%) Ex. Structure at 31 ppm CMP9

18* CMP10

27 *arithmetic mean of 2 tests

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP8.

Ex. Structure I.080

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP8 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compound I.080 was shown to exhibit an efficacy of at least 90% whereas CMP8 was shown to exhibit an efficacy below 10% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP9.

Ex. Structure I.095

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP9 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compounds I.095 were shown to exhibit an efficacy of at least 90% whereas CMP9 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP9 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compounds I.095 were shown to exhibit an efficacy of at least 70% whereas CMP9 was shown to exhibit an efficacy below 20% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP10.

Ex. Structure I.032

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP10 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compound I.032 was shown to exhibit an efficacy of at least 90% whereas CMP10 was shown to exhibit an efficacy below 30% at the same concentration.

Example Q: Comparative Examples

Compounds CMP9, CMP11 and CMP12 were tested in an in vivo preventive test on Pseudomonas syringae pv. tomato (bacterial speck on tomato) the same conditions as described in Example F. Compounds CMP9, CMP11 and CMP12 were prepared in accordance with the teaching of WO2004/024692.

The results are as shown in the tables below.

Efficacy (%) at Ex. Structure 125 ppm CMP9

34* CMP11

 3 *arithmetic mean of 2 tests

Efficacy (%) Ex. Structure at 31 ppm CMP12

10

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP9.

Ex. Structure I.095

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP9 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compound I.095 was shown to exhibit an efficacy of at least 70% whereas CMP10 was shown to exhibit an efficacy below 40% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP11.

Ex. Structure I.083

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP11 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compound I.083 was shown to exhibit an efficacy of at least 70% whereas CMP11 was shown to exhibit an efficacy below 10% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP12.

Ex. Structure I.122

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP12 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compound I.122 was shown to exhibit an efficacy of at least 70% whereas CMP12 was shown to exhibit an efficacy of 10% at the same concentration.

Example R: Comparative Examples

Compounds CMP9 and CMP10 were tested in an in vivo preventive test on Uromyces appendiculatus (bean rust) in the same conditions as described in Example E.

Compounds CMP9 and CMP10 were prepared in accordance with the teaching of WO2004/024692. The results are as shown in the tables below.

Efficacy (%) Ex. Structure at 125 ppm CMP9

33* *arithmetic mean of 2 tests

Efficacy (%) Ex. Structure at 31 ppm CMP10

0

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP9.

Ex. Structure 1.095

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP9 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compound I.095 was shown to exhibit an efficacy of at least 90% whereas CMP9 was shown to exhibit an efficacy below 40% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP10.

Ex. Structure 1.032

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP10 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compound I.032 was shown to exhibit an efficacy of at least 90% whereas CMP10 was shown to exhibit no efficacy at the same concentration.

Example S: Comparative Examples

Compounds CMP10, CMP13, CMP14 and CMP15 were tested in an in vivo preventive test on Peronospora parasitica (Crucifer downy mildew) in the same conditions as described in Example C. Compounds CMP10, CMP13, CMP14 and CMP15 were prepared in accordance with the teaching of WO2004/024692.

The results are as shown in the tables below.

Efficacy (%) Ex. Structure at 125 ppm CMP13

 0 CMP14

 0 CMP15

22 *arithmetic mean of 2 tests

Efficacy (%) Ex. Structure at 31 ppm CMP10

29 CMP14

 0

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP13.

Ex. Structure 1.080

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP13 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compound I.080 was shown to exhibit an efficacy of at least 90% whereas CMP13 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP14.

Ex. Structure 1.032

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP14 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compound I.032 was shown to exhibit an efficacy of at least 90% whereas CMP14 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP14 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compound I.032 was shown to exhibit an efficacy of at least 80% whereas CMP14 was shown to exhibit no efficacy at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP15.

Ex. Structure 1.056

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP15 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compound I.056 was shown to exhibit an efficacy of at least 80% whereas CMP15 was shown to exhibit an efficacy below 30% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP10.

Ex. Structure 1.032

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP10 when tested at a concentration of 31 ppm. More specifically, at a concentration of 31 ppm, compound I.032 was shown to exhibit an efficacy of at least 80% whereas CMP10 was shown to exhibit an efficacy below 30% at the same concentration.

Example T: Comparative Examples

Compounds CMP9, CMP12 and CMP16 were tested in an in vivo preventive test on Colletotrichum lindemuthianum (Anthracnose on bean) in the same conditions as described in Example B.

Compounds CMP9, CMP12 and CMP16 were prepared in accordance with the teaching of WO2004/024692.

The results are as shown in the tables below.

Efficacy (%) Ex. Structure at 500 ppm CMP16

38

Efficacy (%) Ex. Structure at 125 ppm CMP9

30* CMP12

13 *arithmetic mean of 2 tests

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP16.

Ex. Structure 1.136

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP16 when tested at a concentration of 500 ppm. More specifically, at a concentration of 500 ppm, compound I.136 was shown to exhibit an efficacy of at least 80% whereas CMP15 was shown to exhibit an efficacy below 40% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP9.

Ex. Structure 1.095

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP9 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compound I.095 was shown to exhibit an efficacy of at least 70% whereas CMP9 was shown to exhibit an efficacy of 30% at the same concentration.

The compounds of formula (I) of the present invention in the table below were shown to exhibit a better efficacy than structurally related compound CMP12.

Ex. Structure 1.122

The compounds of formula (I) of the present invention were shown to exhibit a better efficacy than structurally related compound CMP12 when tested at a concentration of 125 ppm. More specifically, at a concentration of 125 ppm, compound I.122 was shown to exhibit an efficacy of at least 70% whereas CMP12 was shown to exhibit an efficacy below 20% at the same concentration. 

1. A compound of formula (I):

wherein R¹ and R² are identical and are chlorine or bromine; R³ is methyl; R⁴ and R⁵ are selected independently from one another from the group consisting of hydrogen, halogen, cyano, hydroxyl, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy, C₁-C₆-haloalkyl, —O—C(═O)—C₁-C₆-alkyl, C₃-C₆-carbocycle, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C(═O)—NH₂, —C(═O)—NH(C₁-C₆-alkyl), —C(═O)—N(C₁-C₆-alkyl)₂, —C(═O)—OH, —C(═O)—O—C₁-C₆-alkyl, aryl, 5- to 9-membered heteroaryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy, —C₁-C₆-alkyl-C₁-C₆-haloalkyl, —C₁-C₆-alkyl-C₃-C₆-carbocycle, —C₁-C₆-alkyl-4-, 5- or 6-membered non-aromatic heterocyclyl, —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-hydroxyaryl, —C₁-C₆-alkyl-5- to 9-membered heteroaryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl, —C₁-C₆-alkyl-S—C(═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-C(═O)—NH₂, —C₁-C₆-alkyl-C(═O)—NH(C₁-C₆-alkyl), —C₁-C₆-alkyl-C(═O)—N(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-C(═O)—OH, —C₁-C₆-alkyl-C(═O)—O—C₁-C₆-alkyl, —C₁-C₆-alkyl-NH—C(═NH)—NH₂, —S—C₁-C₆-alkyl, —S—C(═O)—C₁-C₆-alkyl, —S—C(═O)—O—C₁-C₆-alkyl, —S—C(═S)—O—C₁-C₆-alkyl, —S—C(═O)—S—C₁-C₆-alkyl, —S—C(═O)—NH₂, —S—C(═O)—NH(C₁-C₆-alkyl), —S—C(═O)—NH(C₁-C₆-alkyl)₂, —S—C(═S)—NH₂, —S—C(═S)—NH(C₁-C₆-alkyl), —S—C(═S)—NH(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-S—C(═O)—O—C₁-C₆-alkyl, —C₁-C₆-alkyl-S—C(═O)—S—C₁-C₆-alkyl, —C₁-C₆-alkyl-S—C(═O)—NH₂, —C₁-C₆-alkyl-S—C(═O)—NH(C₁-C₆-alkyl), —C₁-C₆-alkyl-S—C(═O)—NH(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-S—C(═S)—NH₂, —C₁-C₆-alkyl-S—C(═S)—NH(C₁-C₆-alkyl), and —C₁-C₆-alkyl-S—C(═S)—NH(C₁-C₆-alkyl)₂, wherein acyclic R⁴ and R⁵ radicals may be substituted with one or more R^(w) substituents, wherein cyclic R⁴ and R⁵ radicals may be substituted with one or more R^(x) substituents, wherein at least one of R⁴ and R⁵ is hydrogen, C₁-C₆-alkyl or C₃-C₆-carbocycle, or R⁴ and R⁵ form, together with the carbon atom to which they are attached, a carbonyl, a thiocarbonyl, a C₃-C₆-carbocycle, or a 3- to 6-membered heterocycle, wherein said C₃-C₆-carbocycle and 3- to 6-membered heterocycle may be substituted with one or more R^(x) substituents; each R^(w) is independently selected from the group consisting of nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ⁶-sulfanyl, formyl, carbamoyl, carbamate, C₃-C₇-cycloalkyl, C₃-C₇-halogenocycloalkyl having 1 to 5 halogen atoms, C₁-C₈-alkylamino, di-C₁-C₈-alkylamino, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, C₁-C₈-alkylsulfanyl, C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbamoyl, di-C₁-C₈-alkylcarbamoyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonyloxy, C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonylamino, C₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C₁-C₈-alkylsulfinyl, C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogen atoms, C₁-C₈-alkylsulfonyl, C₁-C₈-halogenoalkylsulfonyl having 1 to 5 halogen atoms, C₁-C₈-alkylsulfonylamino, C₁-C₈-halogenoalkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, C₁-C₈-alkylsulfamoyl, and di-C₁-C₈-alkylsulfamoyl; each R^(x) is independently selected from the group consisting of halogen, nitro, hydroxyl, cyano, carboxyl, amino, sulfanyl, pentafluoro-λ⁶-sulfanyl, formyl, carbamoyl, carbamate, C₁-C₈-alkyl, C₃-C₇-cycloalkyl, C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, C₃-C₇-halogenocycloalkyl having 1 to 5 halogen atoms, C₂-C₈-alkenyl, C₂-C₈-alkynyl, C₁-C₈-alkylamino, di-C₁-C₈-alkylamino, C₁-C₈-alkoxy, C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, C₁-C₈-alkylsulfanyl, C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonyl, C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbamoyl, di-C₁-C₈-alkylcarbamoyl, C₁-C₈-alkoxycarbonyl, C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonyloxy, C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, C₁-C₈-alkylcarbonylamino, C₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, C₁-C₈-alkylsulfanyl, C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, C₁-C₈-alkylsulfinyl, C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogen atoms, C₁-C₈-alkylsulfonyl, C₁-C₈-halogenoalkylsulfonyl having 1 to 5 halogen atoms, C₁-C₈-alkylsulfonylamino, C₁-C₈-halogenoalkylsulfonylamino having 1 to 5 halogen atoms, sulfamoyl, C₁-C₈-alkylsulfamoyl, and di-C₁-C₈-alkylsulfamoyl; R⁶ and R⁷ are independently selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₃-C₆-carbocycle, or R⁶ and R⁷ form, together with the carbon atom to which they are attached, a C₃-C₆-carbocycle or a 3- to 6-membered heterocycle; n is 0 or 1; W is oxygen or sulfur; Y is NR⁸, wherein R⁸ is hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, hydroxy, C₁-C₆-alkoxy or C₃-C₆-carbocycle; Z is selected from the group consisting of cyano, —C(═O)—OR^(a), —C(═O)—SR^(a), —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c), and —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a); R^(a) is selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₈-cycloalkyl, aryl, aralkyl, 4-, 5- or 6-membered non-aromatic heterocyclyl, —C₁-C₆-alkyl-Si(C₁-C₆-alkyl)₃, —C₁-C₆-alkyl-C₃-C₈-cycloalkyl, 5- to 9-membered heteroaryl, and —C₁-C₆-alkyl-5- to 9-membered heteroaryl, or R^(a) forms, together with R⁴ and with the atoms to which they are attached, a 4- to 7-membered heterocycle; R^(b) and R^(c) are independently selected from the group consisting of hydrogen, C₁-C₆-alkyl, hydroxyl, C₁-C₆-alkoxy, cyano, and C₁-C₆-cyanoalkyl, or R^(b) forms, together with R⁴ and with the atoms to which they are attached, a 4- to 7-membered heterocycle; R^(d) and R^(e) are independently selected from the group consisting of hydrogen, cyano, hydroxyl, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₁-C₆-alkoxy, —O—C(═O)—C₁-C₆-alkyl, C₃-C₆-carbocycle, —C(═O)—NH₂, —C(═O)—NH(C₁-C₆-alkyl), —C(═O)—N(C₁-C₆-alkyl)₂, —C(═O)—OH, —C(═O)—O—C₁-C₆-alkyl, aryl, 5- to 9-membered heteroaryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy, —C₁-C₆-alkyl-C₃-C₆-carbocycle, —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-hydroxyaryl, —C₁-C₆-alkyl-5- to 9-membered heteroaryl, —C₁-C₆-alkyl-S—C₁-C₆-alkyl, —C₁-C₆-alkyl-S—C(═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-C(═O)—NH₂, —C₁-C₆-alkyl-C(═O)—NH(C₁-C₆-alkyl), —C₁-C₆-alkyl-C(═O)—N(C₁-C₆-alkyl)₂, —C₁-C₆-alkyl-C(═O)—OH, —C₁-C₆-alkyl-C(═O)—O—C₁-C₆-alkyl, —C₁-C₆-alkyl-NH—C(═NH)—NH₂, wherein at least one of R^(d) and R^(e) is hydrogen, C₁-C₆-alkyl, or C₃-C₆-carbocycle, or R^(d) and R^(e) form, together with the carbon atom to which they are attached, a carbonyl, C₃-C₆-carbocycle, or a 3- to 6-membered heterocycle; wherein if W is oxygen, Y is NH, n=0, and R⁴ is hydrogen, C₁-C₆-alkyl, —C₁-C₆-alkyl-aryl, —C₁-C₆-alkyl-hydroxyaryl, or —C₁-C₆-alkyl-S—C₁-C₆-alkyl, and R⁵ is hydrogen, or R⁴ and R⁵ form together with the carbon atom to which they are attached a cyclopropyl, then Z is selected from the group consisting of cyano, —C(═O)—SR^(a), —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c), —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a); provided that the compound is not ethyl {[(4,5-dibromo-3-methyl-2-thienyl)carbonyl]amino}(phenyl)acetate or ethyl {[(4,5-dichloro-3-methyl-2-thienyl)carbonyl]amino}(phenyl)acetate.
 2. The compound according to claim 1, wherein R¹ and R² are chlorine; and R³ is methyl.
 3. The compound according to claim 1, wherein R¹ and R² are bromine; and R³ is methyl.
 4. The compound of claim 1, wherein R⁴ and R⁵ are independently selected from the group consisting of hydrogen, C₁-C₆-alkyl, C₁-C₆-hydroxyalkyl, C₃-C₆-carbocycle, aryl, —C₁-C₆-alkyl-C₁-C₆-alkoxy, —C₁-C₆-alkyl-C₃-C₆-carbocycle, C₁-C₆-alkyl-O—(C═O)—C₁-C₆-alkyl, —C₁-C₆-alkyl-C(═O)—OH; —C₁-C₆-alkyl-aryl, and —C₁-C₆-alkyl-S—C₁-C₆-alkyl, wherein acyclic R₄ and R₅ radicals may be substituted with one or more R^(w) substituents, cyclic R⁴ and R⁵ radicals may be substituted with one or more R^(x) substituents, and at least one of R⁴ and R⁵ is hydrogen, C₁-C₆-alkyl, or C₃-C₆-carbocycle, or R⁴ and R⁵ form, together with the carbon atom to which they are attached, a C₃-C₆-carbocycle or a 3- to 6-membered heterocycle, wherein said C₃-C₆-carbocycle and 3- to 6-membered heterocycle may be substituted with one or more R^(x) substituents.
 5. The compound of claim 1, wherein W is oxygen.
 6. The compound of claim 1, wherein Y is NR⁸, wherein R⁸ is C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₁-C₆-cyanoalkyl, hydroxy, C₁-C₆-alkoxy, or C₃-C₆-carbocycle.
 7. The compound of claim 1, wherein Z is selected from the group consisting of cyano, —C(═O)—SR^(a), —C(═O)—NR^(b)R^(c), —C(═S)—NR^(b)R^(c), and —C(═O)—NH—CR^(d)R^(e)—C(═O)—OR^(a).
 8. A composition comprising at least one compound of claim 1, to and at least one agriculturally suitable auxiliary.
 9. A method for controlling bacterial and/or fungal diseases in plants comprising the step of applying at least one compound of claim 1 to a plant, plant part, seed, fruit, or soil in which a plant grows.
 10. (canceled)
 11. The compound of claim 1, wherein R⁸ is hydrogen.
 12. The compound of claim 1, wherein Z is C(═O)—OR^(a).
 13. A method for controlling bacterial and/or fungal diseases in plants comprising the step of applying a composition according to claim 8 to a plant, plant part, seed, fruit, or soil in which a plant grows. 